diff --git a/.github/workflows/unit-tests.yml b/.github/workflows/unit-tests.yml
index 6410f2edd6175..2938ea6302057 100644
--- a/.github/workflows/unit-tests.yml
+++ b/.github/workflows/unit-tests.yml
@@ -30,56 +30,10 @@ jobs:
         # Prevent the include jobs from overriding other jobs
         pattern: [""]
         include:
-          - name: "Downstream Compat"
-            env_file: actions-311-downstream_compat.yaml
-            pattern: "not slow and not network and not single_cpu"
-            pytest_target: "pandas/tests/test_downstream.py"
-          - name: "Minimum Versions"
-            env_file: actions-39-minimum_versions.yaml
-            pattern: "not slow and not network and not single_cpu"
-          - name: "Locale: it_IT"
-            env_file: actions-311.yaml
-            pattern: "not slow and not network and not single_cpu"
-            extra_apt: "language-pack-it"
-            # Use the utf8 version as the default, it has no bad side-effect.
-            lang: "it_IT.utf8"
-            lc_all: "it_IT.utf8"
-            # Also install it_IT (its encoding is ISO8859-1) but do not activate it.
-            # It will be temporarily activated during tests with locale.setlocale
-            extra_loc: "it_IT"
-          - name: "Locale: zh_CN"
-            env_file: actions-311.yaml
-            pattern: "not slow and not network and not single_cpu"
-            extra_apt: "language-pack-zh-hans"
-            # Use the utf8 version as the default, it has no bad side-effect.
-            lang: "zh_CN.utf8"
-            lc_all: "zh_CN.utf8"
-            # Also install zh_CN (its encoding is gb2312) but do not activate it.
-            # It will be temporarily activated during tests with locale.setlocale
-            extra_loc: "zh_CN"
-          - name: "Copy-on-Write 3.9"
-            env_file: actions-39.yaml
-            pattern: "not slow and not network and not single_cpu"
-            pandas_copy_on_write: "1"
-          - name: "Copy-on-Write 3.10"
-            env_file: actions-310.yaml
-            pattern: "not slow and not network and not single_cpu"
-            pandas_copy_on_write: "1"
-          - name: "Copy-on-Write 3.11"
-            env_file: actions-311.yaml
-            pattern: "not slow and not network and not single_cpu"
-            pandas_copy_on_write: "1"
-          - name: "Pypy"
+          - name: "PyPy"
             env_file: actions-pypy-39.yaml
             pattern: "not slow and not network and not single_cpu"
             test_args: "--max-worker-restart 0"
-          - name: "Numpy Dev"
-            env_file: actions-311-numpydev.yaml
-            pattern: "not slow and not network and not single_cpu"
-            test_args: "-W error::DeprecationWarning -W error::FutureWarning"
-          - name: "Pyarrow Nightly"
-            env_file: actions-311-pyarrownightly.yaml
-            pattern: "not slow and not network and not single_cpu"
       fail-fast: false
     name: ${{ matrix.name || format('ubuntu-latest {0}', matrix.env_file) }}
     env:
@@ -160,7 +114,7 @@ jobs:
 
     - name: Test (not single_cpu)
       uses: ./.github/actions/run-tests
-      if: ${{ matrix.name != 'Pypy' }}
+      if: ${{ matrix.name != 'PyPy' }}
       env:
         # Set pattern to not single_cpu if not already set
         PATTERN: ${{ env.PATTERN == '' && 'not single_cpu' || matrix.pattern }}
@@ -170,184 +124,6 @@ jobs:
       env:
         PATTERN: 'single_cpu'
         PYTEST_WORKERS: 0
-      if: ${{ matrix.pattern == '' && (always() && steps.build.outcome == 'success')}}
-
-  macos-windows:
-    timeout-minutes: 180
-    strategy:
-      matrix:
-        os: [macos-latest, windows-latest]
-        env_file: [actions-39.yaml, actions-310.yaml, actions-311.yaml]
-      fail-fast: false
-    runs-on: ${{ matrix.os }}
-    name: ${{ format('{0} {1}', matrix.os, matrix.env_file) }}
-    concurrency:
-      # https://github.community/t/concurrecy-not-work-for-push/183068/7
-      group: ${{ github.event_name == 'push' && github.run_number || github.ref }}-${{ matrix.env_file }}-${{ matrix.os }}
-      cancel-in-progress: true
-    env:
-      PANDAS_CI: 1
-      PYTEST_TARGET: pandas
-      PATTERN: "not slow and not db and not network and not single_cpu"
-      # GH 47443: PYTEST_WORKERS > 0 crashes Windows builds with memory related errors
-      PYTEST_WORKERS: ${{ matrix.os == 'macos-latest' && 'auto' || '0' }}
-
-    steps:
-      - name: Checkout
-        uses: actions/checkout@v3
-        with:
-          fetch-depth: 0
-
-      - name: Set up Conda
-        uses: ./.github/actions/setup-conda
-        with:
-          environment-file: ci/deps/${{ matrix.env_file }}
-
-      - name: Build Pandas
-        uses: ./.github/actions/build_pandas
-
-      - name: Test
-        uses: ./.github/actions/run-tests
-
-  Linux-32-bit:
-    runs-on: ubuntu-22.04
-    container:
-      image: quay.io/pypa/manylinux2014_i686
-      options: --platform linux/386
-    steps:
-      - name: Checkout pandas Repo
-        # actions/checkout does not work since it requires node
-        run: |
-          git config --global --add safe.directory $PWD
-
-          if [ $GITHUB_EVENT_NAME != pull_request ]; then
-              git clone --recursive --branch=$GITHUB_REF_NAME https://github.com/${GITHUB_REPOSITORY}.git $GITHUB_WORKSPACE
-              git reset --hard $GITHUB_SHA
-          else
-              git clone --recursive https://github.com/${GITHUB_REPOSITORY}.git $GITHUB_WORKSPACE
-              git fetch origin $GITHUB_REF:my_ref_name
-              git checkout $GITHUB_BASE_REF
-              git -c user.email="you@example.com" merge --no-commit my_ref_name
-          fi
-      - name: Build environment and Run Tests
-        run: |
-          /opt/python/cp311-cp311/bin/python -m venv ~/virtualenvs/pandas-dev
-          . ~/virtualenvs/pandas-dev/bin/activate
-          python -m pip install --no-cache-dir -U pip wheel setuptools meson[ninja]==1.0.1 meson-python==0.13.1
-          python -m pip install --no-cache-dir versioneer[toml] "cython<3.0.1" numpy python-dateutil pytz pytest>=7.3.2 pytest-xdist>=2.2.0 pytest-asyncio>=0.17 hypothesis>=6.46.1
-          python -m pip install --no-cache-dir --no-build-isolation -e .
-          python -m pip list --no-cache-dir
-          export PANDAS_CI=1
-          python -m pytest -m 'not slow and not network and not clipboard and not single_cpu' pandas --junitxml=test-data.xml
-    concurrency:
-      # https://github.community/t/concurrecy-not-work-for-push/183068/7
-      group: ${{ github.event_name == 'push' && github.run_number || github.ref }}-32bit
-      cancel-in-progress: true
-
-  Linux-Musl:
-    runs-on: ubuntu-22.04
-    container:
-      image: quay.io/pypa/musllinux_1_1_x86_64
-    steps:
-      - name: Checkout pandas Repo
-        # actions/checkout does not work since it requires node
-        run: |
-          git config --global --add safe.directory $PWD
-
-          if [ $GITHUB_EVENT_NAME != pull_request ]; then
-              git clone --recursive --branch=$GITHUB_REF_NAME https://github.com/${GITHUB_REPOSITORY}.git $GITHUB_WORKSPACE
-              git reset --hard $GITHUB_SHA
-          else
-              git clone --recursive https://github.com/${GITHUB_REPOSITORY}.git $GITHUB_WORKSPACE
-              git fetch origin $GITHUB_REF:my_ref_name
-              git checkout $GITHUB_BASE_REF
-              git -c user.email="you@example.com" merge --no-commit my_ref_name
-          fi
-      - name: Configure System Packages
-        run: |
-          apk update
-          apk add musl-locales
-      - name: Build environment
-        run: |
-          /opt/python/cp311-cp311/bin/python -m venv ~/virtualenvs/pandas-dev
-          . ~/virtualenvs/pandas-dev/bin/activate
-          python -m pip install --no-cache-dir -U pip wheel setuptools meson-python==0.13.1 meson[ninja]==1.0.1
-          python -m pip install --no-cache-dir versioneer[toml] "cython<3.0.1" numpy python-dateutil pytz pytest>=7.3.2 pytest-xdist>=2.2.0 pytest-asyncio>=0.17 hypothesis>=6.46.1
-          python -m pip install --no-cache-dir --no-build-isolation -e .
-          python -m pip list --no-cache-dir
-
-      - name: Run Tests
-        run: |
-          . ~/virtualenvs/pandas-dev/bin/activate
-          export PANDAS_CI=1
-          python -m pytest -m 'not slow and not network and not clipboard and not single_cpu' pandas --junitxml=test-data.xml
-    concurrency:
-      # https://github.community/t/concurrecy-not-work-for-push/183068/7
-      group: ${{ github.event_name == 'push' && github.run_number || github.ref }}-musl
-      cancel-in-progress: true
-
-  python-dev:
-    # This job may or may not run depending on the state of the next
-    # unreleased Python version. DO NOT DELETE IT.
-    #
-    # In general, this will remain frozen(present, but not running) until:
-    #    - The next unreleased Python version has released beta 1
-    #      - This version should be available on GitHub Actions.
-    #    - Our required build/runtime dependencies(numpy, pytz, Cython, python-dateutil)
-    #      support that unreleased Python version.
-    #    To unfreeze, comment out the ``if: false`` condition, and make sure you update
-    #    the name of the workflow and Python version in actions/setup-python ``python-version:``
-    #
-    # After it has been unfrozen, this file should remain unfrozen(present, and running) until:
-    #    - The next Python version has been officially released.
-    #    OR
-    #    - Most/All of our optional dependencies support the next Python version AND
-    #    - The next Python version has released a rc(we are guaranteed a stable ABI).
-    #    To freeze this file, uncomment out the ``if: false`` condition, and migrate the jobs
-    #    to the corresponding posix/windows-macos/sdist etc. workflows.
-    # Feel free to modify this comment as necessary.
-    #if: false # Uncomment this to freeze the workflow, comment it to unfreeze
-    defaults:
-      run:
-        shell: bash -eou pipefail {0}
-    runs-on: ${{ matrix.os }}
-    strategy:
-      fail-fast: false
-      matrix:
-        os: [ubuntu-22.04, macOS-latest, windows-latest]
-
-    timeout-minutes: 180
-
-    concurrency:
-      #https://github.community/t/concurrecy-not-work-for-push/183068/7
-      group: ${{ github.event_name == 'push' && github.run_number || github.ref }}-${{ matrix.os }}-${{ matrix.pytest_target }}-dev
-      cancel-in-progress: true
-
-    env:
-      PYTEST_WORKERS: "auto"
-      PANDAS_CI: 1
-      PATTERN: "not slow and not network and not clipboard and not single_cpu"
-      PYTEST_TARGET: pandas
-
-    steps:
-      - uses: actions/checkout@v3
-        with:
-          fetch-depth: 0
-
-      - name: Set up Python Dev Version
-        uses: actions/setup-python@v4
-        with:
-          python-version: '3.12-dev'
+      if: ${{ (matrix.pattern == '' && (always() && steps.build.outcome == 'success')) || matrix.name == 'PyPy'}}
 
-      - name: Build Environment
-        run: |
-          python --version
-          python -m pip install --upgrade pip setuptools wheel meson[ninja]==1.0.1 meson-python==0.13.1
-          python -m pip install --pre --extra-index-url https://pypi.anaconda.org/scientific-python-nightly-wheels/simple numpy
-          python -m pip install versioneer[toml]
-          python -m pip install python-dateutil pytz tzdata "cython<3.0.1" hypothesis>=6.46.1 pytest>=7.3.2 pytest-xdist>=2.2.0 pytest-cov pytest-asyncio>=0.17
-          python -m pip install -ve . --no-build-isolation --no-index
-          python -m pip list
 
-      - name: Run Tests
-        uses: ./.github/actions/run-tests
diff --git a/ci/deps/actions-pypy-39.yaml b/ci/deps/actions-pypy-39.yaml
index 23c3706f43dad..f2f60d41d22a3 100644
--- a/ci/deps/actions-pypy-39.yaml
+++ b/ci/deps/actions-pypy-39.yaml
@@ -15,7 +15,7 @@ dependencies:
 
   # test dependencies
   - pytest>=7.3.2
-  - pytest-cov
+  # - pytest-cov  # Don't use coverage on PyPy, it is too slow
   - pytest-asyncio>=0.17.0
   - pytest-xdist>=2.2.0
   - hypothesis>=6.46.1
diff --git a/ci/run_tests.sh b/ci/run_tests.sh
index 48ef21686a26f..1df767cca7fad 100755
--- a/ci/run_tests.sh
+++ b/ci/run_tests.sh
@@ -8,7 +8,10 @@ export PYTHONHASHSEED=$(python -c 'import random; print(random.randint(1, 429496
 # May help reproduce flaky CI builds if set in subsequent runs
 echo PYTHONHASHSEED=$PYTHONHASHSEED
 
-COVERAGE="-s --cov=pandas --cov-report=xml --cov-append --cov-config=pyproject.toml"
+export IS_PYPY=$(python -c "import sys; print(sys.implementation.name == 'pypy')")
+if [[ "$IS_PYPY" != "True" ]]; then
+  COVERAGE="-s --cov=pandas --cov-report=xml --cov-append --cov-config=pyproject.toml"
+fi
 
 PYTEST_CMD="MESONPY_EDITABLE_VERBOSE=1 PYTHONDEVMODE=1 PYTHONWARNDEFAULTENCODING=1 pytest -r fEs -n $PYTEST_WORKERS --dist=loadfile $TEST_ARGS $COVERAGE $PYTEST_TARGET"
 
diff --git a/pandas/_testing/__init__.py b/pandas/_testing/__init__.py
index 73835252c0329..2d3859d8f58d9 100644
--- a/pandas/_testing/__init__.py
+++ b/pandas/_testing/__init__.py
@@ -8,7 +8,7 @@
 import os
 import re
 import string
-from sys import byteorder
+from sys import byteorder, implementation
 from typing import (
     TYPE_CHECKING,
     Callable,
@@ -210,6 +210,9 @@
     ]
 ]
 
+IS_PYPY = implementation.name == 'pypy'
+
+
 if not pa_version_under7p0:
     import pyarrow as pa
 
@@ -1127,6 +1130,7 @@ def shares_memory(left, right) -> bool:
     "iat",
     "iloc",
     "index_subclass_makers_generator",
+    "IS_PYPY",
     "loc",
     "makeBoolIndex",
     "makeCategoricalIndex",
diff --git a/pandas/testing.py b/pandas/testing.py
index 841b55df48556..f2044d51bc6b8 100644
--- a/pandas/testing.py
+++ b/pandas/testing.py
@@ -8,6 +8,7 @@
     assert_frame_equal,
     assert_index_equal,
     assert_series_equal,
+    IS_PYPY,
 )
 
 __all__ = [
@@ -15,4 +16,5 @@
     "assert_frame_equal",
     "assert_series_equal",
     "assert_index_equal",
+    "IS_PYPY",
 ]
diff --git a/pandas/tests/apply/test_invalid_arg.py b/pandas/tests/apply/test_invalid_arg.py
index a3d9de5e78afb..2ef0d4a116d4b 100644
--- a/pandas/tests/apply/test_invalid_arg.py
+++ b/pandas/tests/apply/test_invalid_arg.py
@@ -220,7 +220,10 @@ def transform2(row):
 )
 def test_agg_cython_table_raises_frame(df, func, expected, axis):
     # GH 21224
-    msg = "can't multiply sequence by non-int of type 'str'"
+    if tm.IS_PYPY:
+        msg = "unsupported operand type(s) for"
+    else:
+        msg = "can't multiply sequence by non-int of type 'str'"
     warn = None if isinstance(func, str) else FutureWarning
     with pytest.raises(expected, match=msg):
         with tm.assert_produces_warning(warn, match="using DataFrame.cumprod"):
@@ -246,6 +249,8 @@ def test_agg_cython_table_raises_frame(df, func, expected, axis):
 def test_agg_cython_table_raises_series(series, func, expected):
     # GH21224
     msg = r"[Cc]ould not convert|can't multiply sequence by non-int of type"
+    if tm.IS_PYPY:
+        msg += "|unsupported operand type(s) for"
     if func == "median" or func is np.nanmedian or func is np.median:
         msg = r"Cannot convert \['a' 'b' 'c'\] to numeric"
     warn = None if isinstance(func, str) else FutureWarning
diff --git a/pandas/tests/arithmetic/test_datetime64.py b/pandas/tests/arithmetic/test_datetime64.py
index 34b526bf97408..c1f20b2b860ed 100644
--- a/pandas/tests/arithmetic/test_datetime64.py
+++ b/pandas/tests/arithmetic/test_datetime64.py
@@ -1302,7 +1302,8 @@ def test_dti_add_tick_tzaware(self, tz_aware_fixture, box_with_array):
             tm.assert_equal(roundtrip, dates)
 
             msg = "|".join(
-                ["bad operand type for unary -", "cannot subtract DatetimeArray"]
+                ["bad operand type for unary -", "cannot subtract DatetimeArray",
+                 "unsupported operand type for unary"]  # PyPy
             )
             with pytest.raises(TypeError, match=msg):
                 scalar - dates
@@ -1919,7 +1920,10 @@ def test_datetime64_ops_nat(self):
 
         # subtraction
         tm.assert_series_equal(-NaT + datetime_series, nat_series_dtype_timestamp)
-        msg = "bad operand type for unary -: 'DatetimeArray'"
+        if tm.IS_PYPY:
+            msg = "unsupported operand type for unary"
+        else:
+            msg = "bad operand type for unary -: 'DatetimeArray'"
         with pytest.raises(TypeError, match=msg):
             -single_nat_dtype_datetime + datetime_series
 
diff --git a/pandas/tests/arithmetic/test_period.py b/pandas/tests/arithmetic/test_period.py
index 2a34566d2f9f5..106f1e39d342f 100644
--- a/pandas/tests/arithmetic/test_period.py
+++ b/pandas/tests/arithmetic/test_period.py
@@ -1007,7 +1007,10 @@ def test_pi_sub_intarray(self, int_holder):
         expected = PeriodIndex([Period("2014Q1"), Period("NaT")])
         tm.assert_index_equal(result, expected)
 
-        msg = r"bad operand type for unary -: 'PeriodArray'"
+        if tm.IS_PYPY:
+            msg = "unsupported operand type for unary"
+        else:
+            msg = r"bad operand type for unary -: 'PeriodArray'"
         with pytest.raises(TypeError, match=msg):
             other - pi
 
@@ -1043,6 +1046,7 @@ def test_parr_add_timedeltalike_minute_gt1(self, three_days, box_with_array):
             [
                 r"bad operand type for unary -: 'PeriodArray'",
                 r"cannot subtract PeriodArray from timedelta64\[[hD]\]",
+                "unsupported operand type for unary",  # PyPy
             ]
         )
         with pytest.raises(TypeError, match=msg):
@@ -1075,6 +1079,7 @@ def test_parr_add_timedeltalike_tick_gt1(self, three_days, freqstr, box_with_arr
             [
                 r"bad operand type for unary -: 'PeriodArray'",
                 r"cannot subtract PeriodArray from timedelta64\[[hD]\]",
+                "unsupported operand type for unary",  # PyPy
             ]
         )
         with pytest.raises(TypeError, match=msg):
diff --git a/pandas/tests/arrays/floating/test_arithmetic.py b/pandas/tests/arrays/floating/test_arithmetic.py
index 056c22d8c1131..3e4d46b00991a 100644
--- a/pandas/tests/arrays/floating/test_arithmetic.py
+++ b/pandas/tests/arrays/floating/test_arithmetic.py
@@ -140,6 +140,7 @@ def test_error_invalid_values(data, all_arithmetic_operators):
             "ufunc '.*' not supported for the input types, and the inputs could not",
             "ufunc '.*' did not contain a loop with signature matching types",
             "Concatenation operation is not implemented for NumPy arrays",
+            r"unsupported operand type(s) for",  # PyPy
         ]
     )
     with pytest.raises(TypeError, match=msg):
@@ -161,6 +162,7 @@ def test_error_invalid_values(data, all_arithmetic_operators):
             "not all arguments converted during string formatting",
             "can't multiply sequence by non-int of type 'float'",
             "ufunc 'subtract' cannot use operands with types dtype",
+            r"unsupported operand type(s) for",  # PyPy
             (
                 "ufunc 'add' cannot use operands with types "
                 rf"dtype\('{tm.ENDIAN}M8\[ns\]'\)"
diff --git a/pandas/tests/computation/test_eval.py b/pandas/tests/computation/test_eval.py
index 9c630e29ea8e6..3a42557f95cab 100644
--- a/pandas/tests/computation/test_eval.py
+++ b/pandas/tests/computation/test_eval.py
@@ -401,7 +401,10 @@ def test_frame_invert(self, engine, parser):
             with pytest.raises(ValueError, match="unknown type object"):
                 pd.eval(expr, engine=engine, parser=parser)
         else:
-            msg = "bad operand type for unary ~: 'str'"
+            if tm.IS_PYPY:
+                msg = "unsupported operand type for unary"
+            else:
+                msg = "bad operand type for unary ~: 'str'"
             with pytest.raises(TypeError, match=msg):
                 pd.eval(expr, engine=engine, parser=parser)
 
@@ -448,7 +451,10 @@ def test_series_invert(self, engine, parser):
             with pytest.raises(ValueError, match="unknown type object"):
                 pd.eval(expr, engine=engine, parser=parser)
         else:
-            msg = "bad operand type for unary ~: 'str'"
+            if tm.IS_PYPY:
+                msg = "unsupported operand type for unary"
+            else:
+                msg = "bad operand type for unary ~: 'str'"
             with pytest.raises(TypeError, match=msg):
                 pd.eval(expr, engine=engine, parser=parser)
 
@@ -541,7 +547,10 @@ def test_series_pos(self, lhs, engine, parser):
         tm.assert_series_equal(expect, result)
 
     def test_scalar_unary(self, engine, parser):
-        msg = "bad operand type for unary ~: 'float'"
+        if tm.IS_PYPY:
+            msg = "unsupported operand type for unary"
+        else:
+            msg = "bad operand type for unary ~: 'float'"
         with pytest.raises(TypeError, match=msg):
             pd.eval("~1.0", engine=engine, parser=parser)
 
diff --git a/pandas/tests/frame/test_reductions.py b/pandas/tests/frame/test_reductions.py
index e7b6a0c0b39b0..e487a3f82d5f5 100644
--- a/pandas/tests/frame/test_reductions.py
+++ b/pandas/tests/frame/test_reductions.py
@@ -177,10 +177,10 @@ def test_stat_op_api_float_string_frame(self, float_string_frame, axis, opname):
             if opname in ["var", "std", "sem", "skew", "kurt"]:
                 msg = "could not convert string to float: 'bar'"
             elif opname == "product":
-                if axis == 1:
-                    msg = "can't multiply sequence by non-int of type 'float'"
+                if tm.IS_PYPY:
+                    msg = "unsupported operand type"
                 else:
-                    msg = "can't multiply sequence by non-int of type 'str'"
+                    msg = "can't multiply sequence by non-int of type"
             elif opname == "sum":
                 msg = r"unsupported operand type\(s\) for \+: 'float' and 'str'"
             elif opname == "mean":
diff --git a/pandas/tests/frame/test_unary.py b/pandas/tests/frame/test_unary.py
index 5e29d3c868983..5befb14109fcc 100644
--- a/pandas/tests/frame/test_unary.py
+++ b/pandas/tests/frame/test_unary.py
@@ -51,7 +51,8 @@ def test_neg_object(self, df, expected):
     def test_neg_raises(self, df):
         msg = (
             "bad operand type for unary -: 'str'|"
-            r"bad operand type for unary -: 'DatetimeArray'"
+            r"bad operand type for unary -: 'DatetimeArray'|"
+            "unsupported operand type for unary"  # PyPy
         )
         with pytest.raises(TypeError, match=msg):
             (-df)
@@ -131,9 +132,12 @@ def test_pos_object(self, df):
     def test_pos_object_raises(self, df):
         # GH#21380
         if np_version_gte1p25:
+            if tm.IS_PYPY:
+                msg = "unsupported operand type for unary"
+            else:
+                msg = r"^bad operand type for unary \+: \'str\'$"
             with pytest.raises(
-                TypeError, match=r"^bad operand type for unary \+: \'str\'$"
-            ):
+                TypeError, match=msg):
                 tm.assert_frame_equal(+df, df)
         else:
             tm.assert_series_equal(+df["a"], df["a"])
@@ -142,7 +146,10 @@ def test_pos_object_raises(self, df):
         "df", [pd.DataFrame({"a": pd.to_datetime(["2017-01-22", "1970-01-01"])})]
     )
     def test_pos_raises(self, df):
-        msg = r"bad operand type for unary \+: 'DatetimeArray'"
+        if tm.IS_PYPY:
+            msg = "unsupported operand type for unary"
+        else:
+            msg = r"bad operand type for unary \+: 'DatetimeArray'"
         with pytest.raises(TypeError, match=msg):
             (+df)
         with pytest.raises(TypeError, match=msg):
diff --git a/pandas/tests/groupby/test_filters.py b/pandas/tests/groupby/test_filters.py
index 0bb7ad4fd274d..998a1e4bd5ad5 100644
--- a/pandas/tests/groupby/test_filters.py
+++ b/pandas/tests/groupby/test_filters.py
@@ -157,7 +157,10 @@ def test_filter_bad_shapes():
         g_s.filter(f)
 
     f = lambda x: np.outer(x, x)
-    msg = "can't multiply sequence by non-int of type 'str'"
+    if tm.IS_PYPY:
+        msg = "unsupported operand type(s) for"
+    else:
+        msg = "can't multiply sequence by non-int of type 'str'"
     with pytest.raises(TypeError, match=msg):
         g_df.filter(f)
     msg = "the filter must return a boolean result"
diff --git a/pandas/tests/libs/test_hashtable.py b/pandas/tests/libs/test_hashtable.py
index b78e6426ca17f..4d0ba413abe36 100644
--- a/pandas/tests/libs/test_hashtable.py
+++ b/pandas/tests/libs/test_hashtable.py
@@ -2,7 +2,10 @@
 from contextlib import contextmanager
 import re
 import struct
-import tracemalloc
+try:
+    import tracemalloc
+except ModuleNotFoundError:
+    tracemalloc = None
 
 import numpy as np
 import pytest
@@ -16,6 +19,8 @@
 
 @contextmanager
 def activated_tracemalloc() -> Generator[None, None, None]:
+    if not tracemalloc:
+        pytest.skip("no tracemalloc available")
     tracemalloc.start()
     try:
         yield
diff --git a/pandas/tests/resample/test_resample_api.py b/pandas/tests/resample/test_resample_api.py
index 1b20a7b99d1d7..d7fdbe65ccd59 100644
--- a/pandas/tests/resample/test_resample_api.py
+++ b/pandas/tests/resample/test_resample_api.py
@@ -865,8 +865,8 @@ def test_end_and_end_day_origin(
         ("sum", False, {"cat": ["cat_1cat_2"], "num": [25]}),
         ("sum", lib.no_default, {"cat": ["cat_1cat_2"], "num": [25]}),
         ("prod", True, {"num": [100]}),
-        ("prod", False, "can't multiply sequence"),
-        ("prod", lib.no_default, "can't multiply sequence"),
+        ("prod", False, r"can't multiply sequence|unsupported operand type\(s\) for"),
+        ("prod", lib.no_default, r"can't multiply sequence|unsupported operand type\(s\) for"),
         ("min", True, {"num": [5]}),
         ("min", False, {"cat": ["cat_1"], "num": [5]}),
         ("min", lib.no_default, {"cat": ["cat_1"], "num": [5]}),
diff --git a/pandas/tests/scalar/interval/test_interval.py b/pandas/tests/scalar/interval/test_interval.py
index a02dbf0a0413f..0e5fbd88e8ce7 100644
--- a/pandas/tests/scalar/interval/test_interval.py
+++ b/pandas/tests/scalar/interval/test_interval.py
@@ -204,7 +204,8 @@ def test_math_mult(self, closed):
         with pytest.raises(TypeError, match=msg):
             interval * interval
 
-        msg = r"can\'t multiply sequence by non-int"
+        msg = (r"can\'t multiply sequence by non-int"
+               r"|unsupported operand type\(s\) for \*")
         with pytest.raises(TypeError, match=msg):
             interval * "foo"
 
diff --git a/pandas/tests/scalar/timedelta/test_timedelta.py b/pandas/tests/scalar/timedelta/test_timedelta.py
index f1d8acf47b29a..fcb1ffd6c430b 100644
--- a/pandas/tests/scalar/timedelta/test_timedelta.py
+++ b/pandas/tests/scalar/timedelta/test_timedelta.py
@@ -330,7 +330,10 @@ class TestTimedeltaUnaryOps:
     def test_invert(self):
         td = Timedelta(10, unit="d")
 
-        msg = "bad operand type for unary ~"
+        if tm.IS_PYPY:
+            msg = "unsupported operand type for unary"
+        else:
+            msg = "bad operand type for unary ~"
         with pytest.raises(TypeError, match=msg):
             ~td