diff --git a/Doc/contents.rst b/Doc/contents.rst
index 852be4a6d5b6ba7..40f9c090e3d00b6 100644
--- a/Doc/contents.rst
+++ b/Doc/contents.rst
@@ -6,19 +6,19 @@
 
    whatsnew/index.rst
    tutorial/index.rst
-   using/index.rst
-   reference/index.rst
    builtins/index.rst
    library/index.rst
+   reference/index.rst
+   howto/index.rst
+   using/index.rst
+   installing/index.rst
    extending/index.rst
    c-api/index.rst
-   installing/index.rst
-   howto/index.rst
    faq/index.rst
    deprecations/index.rst
    glossary.rst
 
-   about.rst
    bugs.rst
-   copyright.rst
    license.rst
+   copyright.rst
+   about.rst
diff --git a/Doc/tools/templates/indexcontent.html b/Doc/tools/templates/indexcontent.html
index 59a693c00003c45..dc2a95fc021b029 100644
--- a/Doc/tools/templates/indexcontent.html
+++ b/Doc/tools/templates/indexcontent.html
@@ -16,17 +16,17 @@
     <meta name="theme-color" content="#3776ab">
     <style>
       .contentstable {
-        display: grid;
+        display: flex;
+        flex-flow: row wrap;
         gap: 0 2em;
-        grid-template-columns: 1fr 1fr;
+        list-style: none;
         margin: 0 auto;
         max-width: 90%;
-      }
-      .contentstable ul {
-        list-style: none;
-        margin: 0;
         padding: 0;
       }
+      .contentstable > li {
+        flex: 0 0 calc(50% - 1em);
+      }
       .contentstable a {
         text-decoration: none;
       }
@@ -38,8 +38,8 @@
         margin-bottom: 1em;
       }
       @media (max-width: 600px) {
-        .contentstable {
-          grid-template-columns: 1fr;
+        .contentstable > li {
+          flex-basis: 100%;
         }
       }
     </style>
@@ -50,84 +50,68 @@ <h1>{{ docstitle|e }}</h1>
   {% trans %}Welcome! This is the official documentation for Python {{ release }}.{% endtrans %}
   </p>
   <p><strong>{% trans %}Documentation sections:{% endtrans %}</strong></p>
-  <div class="contentstable">
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("whatsnew/" + version) }}">{% trans %}What's new in Python {{ version }}?{% endtrans %}</a><br>
-         <span class="linkdescr"> {% trans whatsnew_index=pathto("whatsnew/index") %}Or <a href="{{ whatsnew_index }}">all "What's new" documents since Python 2.0</a>{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("tutorial/index") }}">{% trans %}Tutorial{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Start here: a tour of Python's syntax and features{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("builtins/index") }}">{% trans %}Built-ins reference{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Built-in functions and classes{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("library/index") }}">{% trans %}Library reference{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Standard library modules{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("reference/index") }}">{% trans %}Language reference{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Syntax and language elements{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("using/index") }}">{% trans %}Python setup and usage{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}How to install, configure, and use Python{% endtrans %}</span></li>
-    </ul>
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("howto/index") }}">{% trans %}Python HOWTOs{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}In-depth topic manuals{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("installing/index") }}">{% trans %}Installing Python modules{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Third-party modules and PyPI.org{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("extending/index") }}">{% trans %}Extending and embedding{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}For C/C++ programmers{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("c-api/index") }}">{% trans %}Python's C API{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}C API reference{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("faq/index") }}">{% trans %}FAQs{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Frequently asked questions (with answers!){% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("deprecations/index") }}">{% trans %}Deprecations{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Deprecated functionality{% endtrans %}</span></li>
-    </ul>
-  </div>
+  <ul class="contentstable">
+    <li class="biglink"><a class="biglink" href="{{ pathto("whatsnew/" + version) }}">{% trans %}What's new in Python {{ version }}?{% endtrans %}</a><br>
+       <span class="linkdescr"> {% trans whatsnew_index=pathto("whatsnew/index") %}Or <a href="{{ whatsnew_index }}">all "What's new" documents since Python 2.0</a>{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("tutorial/index") }}">{% trans %}Tutorial{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Start here: a tour of Python's syntax and features{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("builtins/index") }}">{% trans %}Built-ins reference{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Built-in functions and classes{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("library/index") }}">{% trans %}Library reference{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Standard library modules{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("reference/index") }}">{% trans %}Language reference{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Syntax and language elements{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("howto/index") }}">{% trans %}Python HOWTOs{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}In-depth topic manuals{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("using/index") }}">{% trans %}Python setup and usage{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}How to install, configure, and use Python{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("installing/index") }}">{% trans %}Installing Python modules{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Third-party modules and PyPI.org{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("extending/index") }}">{% trans %}Extending and embedding{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}For C/C++ programmers{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("c-api/index") }}">{% trans %}Python's C API{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}C API reference{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("faq/index") }}">{% trans %}FAQs{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Frequently asked questions (with answers!){% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("deprecations/index") }}">{% trans %}Deprecations{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Deprecated functionality{% endtrans %}</span></li>
+  </ul>
 
   <p><strong>{% trans %}Other resources:{% endtrans %}</strong></p>
-  <div class="contentstable">
-    <ul>
-      <li class="biglink"><a class="biglink" href="https://devguide.python.org">{% trans %}Python developer's guide{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Information on contributing to Python{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="https://packaging.python.org">{% trans %}Python Packaging User Guide{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Resources relating to Python packaging{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="https://www.python.org/doc/av/">{% trans %}Audio/visual talks{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Podcasts, talks, and video presentations from the community{% endtrans %}</span></li>
-    </ul>
-    <ul>
-      <li class="biglink"><a class="biglink" href="https://peps.python.org/">{% trans %}Python Enhancement Proposals{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Index of proposed improvements to Python{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="https://typing.python.org">{% trans %}Static Typing with Python{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Information and guides about Python type safety{% endtrans %}</span></li>
-    </ul>
-  </div>
+  <ul class="contentstable">
+    <li class="biglink"><a class="biglink" href="https://devguide.python.org">{% trans %}Python developer's guide{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Information on contributing to Python{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="https://packaging.python.org">{% trans %}Python Packaging User Guide{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Resources relating to Python packaging{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="https://www.python.org/doc/av/">{% trans %}Audio/visual talks{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Podcasts, talks, and video presentations from the community{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="https://peps.python.org/">{% trans %}Python Enhancement Proposals{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Index of proposed improvements to Python{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="https://typing.python.org">{% trans %}Static Typing with Python{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Information and guides about Python type safety{% endtrans %}</span></li>
+  </ul>
 
   <p><strong>{% trans %}Indices, glossary, and search:{% endtrans %}</strong></p>
-  <div class="contentstable">
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("py-modindex") }}">{% trans %}Global module index{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}All modules and libraries{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("genindex") }}">{% trans %}General index{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}All functions, classes, and terms{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("glossary") }}">{% trans %}Glossary{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Terms explained{% endtrans %}</span></li>
-    </ul>
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("search") }}">{% trans %}Search page{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}Search this documentation{% endtrans %}</span></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("contents") }}">{% trans %}Complete table of contents{% endtrans %}</a><br>
-         <span class="linkdescr">{% trans %}All sections and subsections{% endtrans %}</span></li>
-    </ul>
-  </div>
+  <ul class="contentstable">
+    <li class="biglink"><a class="biglink" href="{{ pathto("py-modindex") }}">{% trans %}Global module index{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}All modules and libraries{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("genindex") }}">{% trans %}General index{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}All functions, classes, and terms{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("glossary") }}">{% trans %}Glossary{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Terms explained{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("search") }}">{% trans %}Search page{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}Search this documentation{% endtrans %}</span></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("contents") }}">{% trans %}Complete table of contents{% endtrans %}</a><br>
+       <span class="linkdescr">{% trans %}All sections and subsections{% endtrans %}</span></li>
+  </ul>
 
   <p><strong>{% trans %}Project information:{% endtrans %}</strong></p>
-  <div class="contentstable">
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("bugs") }}">{% trans %}Reporting issues{% endtrans %}</a></li>
-      <li class="biglink"><a class="biglink" href="https://devguide.python.org/documentation/help-documenting/">{% trans %}Contributing to docs{% endtrans %}</a></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("download") }}">{% trans %}Download the documentation{% endtrans %}</a></li>
-    </ul>
-    <ul>
-      <li class="biglink"><a class="biglink" href="{{ pathto("license") }}">{% trans %}History and license of Python{% endtrans %}</a></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("copyright") }}">{% trans %}Copyright{% endtrans %}</a></li>
-      <li class="biglink"><a class="biglink" href="{{ pathto("about") }}">{% trans %}About the documentation{% endtrans %}</a></li>
-    </ul>
-  </div>
+  <ul class="contentstable">
+    <li class="biglink"><a class="biglink" href="{{ pathto("bugs") }}">{% trans %}Reporting issues{% endtrans %}</a></li>
+    <li class="biglink"><a class="biglink" href="https://devguide.python.org/documentation/help-documenting/">{% trans %}Contributing to docs{% endtrans %}</a></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("download") }}">{% trans %}Download the documentation{% endtrans %}</a></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("license") }}">{% trans %}History and license of Python{% endtrans %}</a></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("copyright") }}">{% trans %}Copyright{% endtrans %}</a></li>
+    <li class="biglink"><a class="biglink" href="{{ pathto("about") }}">{% trans %}About the documentation{% endtrans %}</a></li>
+  </ul>
 {% endblock %}