diff --git a/doc/api/crypto.md b/doc/api/crypto.md
index db21651c939abc..67490744c50c8f 100644
--- a/doc/api/crypto.md
+++ b/doc/api/crypto.md
@@ -5813,44 +5813,18 @@ See the [list of SSL OP Flags][] for details.
     <td>Instructs OpenSSL to disable a SSL 3.0/TLS 1.0 vulnerability
     workaround added in OpenSSL 0.9.6d.</td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_EPHEMERAL_RSA</code></td>
-    <td>Instructs OpenSSL to always use the tmp_rsa key when performing RSA
-    operations.</td>
-  </tr>
   <tr>
     <td><code>SSL_OP_LEGACY_SERVER_CONNECT</code></td>
     <td>Allows initial connection to servers that do not support RI.</td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_MICROSOFT_BIG_SSLV3_BUFFER</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_MICROSOFT_SESS_ID_BUG</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_MSIE_SSLV2_RSA_PADDING</code></td>
-    <td>Instructs OpenSSL to disable the workaround for a man-in-the-middle
-    protocol-version vulnerability in the SSL 2.0 server implementation.</td>
-  </tr>
   <tr>
     <td><code>SSL_OP_NETSCAPE_CA_DN_BUG</code></td>
     <td></td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_NETSCAPE_CHALLENGE_BUG</code></td>
-    <td></td>
-  </tr>
   <tr>
     <td><code>SSL_OP_NETSCAPE_DEMO_CIPHER_CHANGE_BUG</code></td>
     <td></td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_NETSCAPE_REUSE_CIPHER_CHANGE_BUG</code></td>
-    <td></td>
-  </tr>
   <tr>
     <td><code>SSL_OP_NO_COMPRESSION</code></td>
     <td>Instructs OpenSSL to disable support for SSL/TLS compression.</td>
@@ -5900,14 +5874,6 @@ See the [list of SSL OP Flags][] for details.
     <td><code>SSL_OP_NO_TLSv1_3</code></td>
     <td>Instructs OpenSSL to turn off TLS v1.3</td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_PKCS1_CHECK_1</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_PKCS1_CHECK_2</code></td>
-    <td></td>
-  </tr>
   <tr>
     <td><code>SSL_OP_PRIORITIZE_CHACHA</code></td>
     <td>Instructs OpenSSL server to prioritize ChaCha20-Poly1305
@@ -5916,32 +5882,6 @@ See the [list of SSL OP Flags][] for details.
     <code>SSL_OP_CIPHER_SERVER_PREFERENCE</code>
     is not enabled.</td>
   </tr>
-  <tr>
-    <td><code>SSL_OP_SINGLE_DH_USE</code></td>
-    <td>Instructs OpenSSL to always create a new key when using
-    temporary/ephemeral DH parameters.</td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_SINGLE_ECDH_USE</code></td>
-    <td>Instructs OpenSSL to always create a new key when using
-    temporary/ephemeral ECDH parameters.</td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_SSLEAY_080_CLIENT_DH_BUG</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_SSLREF2_REUSE_CERT_TYPE_BUG</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_TLS_BLOCK_PADDING_BUG</code></td>
-    <td></td>
-  </tr>
-  <tr>
-    <td><code>SSL_OP_TLS_D5_BUG</code></td>
-    <td></td>
-  </tr>
   <tr>
     <td><code>SSL_OP_TLS_ROLLBACK_BUG</code></td>
     <td>Instructs OpenSSL to disable version rollback attack detection.</td>