diff --git a/superset/charts/commands/delete.py b/superset/charts/commands/delete.py
index cb6644c711c45..4c636f0433a73 100644
--- a/superset/charts/commands/delete.py
+++ b/superset/charts/commands/delete.py
@@ -15,7 +15,7 @@
 # specific language governing permissions and limitations
 # under the License.
 import logging
-from typing import Optional
+from typing import cast, Optional
 
 from flask_appbuilder.models.sqla import Model
 from flask_babel import lazy_gettext as _
@@ -45,8 +45,13 @@ def __init__(self, model_id: int):
 
     def run(self) -> Model:
         self.validate()
+        self._model = cast(Slice, self._model)
         try:
             Dashboard.clear_cache_for_slice(slice_id=self._model_id)
+            # Even though SQLAlchemy should in theory delete rows from the association
+            # table, sporadically Superset will error because the rows are not deleted.
+            # Let's do it manually here to prevent the error.
+            self._model.owners = []
             chart = ChartDAO.delete(self._model)
         except DAODeleteFailedError as ex:
             logger.exception(ex.exception)
diff --git a/superset/datasets/commands/delete.py b/superset/datasets/commands/delete.py
index 6f91567958135..1487f1028b3be 100644
--- a/superset/datasets/commands/delete.py
+++ b/superset/datasets/commands/delete.py
@@ -15,7 +15,7 @@
 # specific language governing permissions and limitations
 # under the License.
 import logging
-from typing import Optional
+from typing import cast, Optional
 
 from flask_appbuilder.models.sqla import Model
 from sqlalchemy.exc import SQLAlchemyError
@@ -43,7 +43,12 @@ def __init__(self, model_id: int):
 
     def run(self) -> Model:
         self.validate()
+        self._model = cast(SqlaTable, self._model)
         try:
+            # Even though SQLAlchemy should in theory delete rows from the association
+            # table, sporadically Superset will error because the rows are not deleted.
+            # Let's do it manually here to prevent the error.
+            self._model.owners = []
             dataset = DatasetDAO.delete(self._model, commit=False)
             db.session.commit()
         except (SQLAlchemyError, DAODeleteFailedError) as ex: