diff --git a/packages/docusaurus-utils/src/__tests__/markdownUtils.test.ts b/packages/docusaurus-utils/src/__tests__/markdownUtils.test.ts
index 34648991ba35..b24f8185c651 100644
--- a/packages/docusaurus-utils/src/__tests__/markdownUtils.test.ts
+++ b/packages/docusaurus-utils/src/__tests__/markdownUtils.test.ts
@@ -438,6 +438,88 @@ Lorem Ipsum
     });
   });
 
+  it('preserves trailing # when not preceded by space (e.g. C# or F#)', () => {
+    const markdownC = dedent`
+
+          # Learn C#
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdownC)).toEqual({
+      content: markdownC,
+      contentTitle: 'Learn C#',
+    });
+
+    const markdownF = dedent`
+
+          # Learn F#
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdownF)).toEqual({
+      content: markdownF,
+      contentTitle: 'Learn F#',
+    });
+  });
+
+  it('preserves trailing # in title with custom anchor id', () => {
+    const markdown = dedent`
+
+          # Learn C# {#learn-csharp}
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdown)).toEqual({
+      content: markdown,
+      contentTitle: 'Learn C#',
+    });
+  });
+
+  it('preserves trailing # in title with closing # sequence', () => {
+    const markdown = dedent`
+
+          # Learn C# #
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdown)).toEqual({
+      content: markdown,
+      contentTitle: 'Learn C#',
+    });
+  });
+
+  it('handles empty heading consisting only of closing hashes', () => {
+    const markdown = dedent`
+
+          # ###
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdown)).toEqual({
+      content: markdown,
+      contentTitle: '',
+    });
+  });
+
+  it('preserves literal trailing hash when followed by custom heading id', () => {
+    const markdown = dedent`
+
+          # Title # {#id}
+
+          Lorem Ipsum
+
+        `;
+    expect(parseMarkdownContentTitle(markdown)).toEqual({
+      content: markdown,
+      contentTitle: 'Title #',
+    });
+  });
+
   it('parses markdown h1 title at the top followed by h2 title', () => {
     const markdown = dedent`
 
diff --git a/packages/docusaurus-utils/src/markdownUtils.ts b/packages/docusaurus-utils/src/markdownUtils.ts
index 3a82a52cbb6e..53719f820c4b 100644
--- a/packages/docusaurus-utils/src/markdownUtils.ts
+++ b/packages/docusaurus-utils/src/markdownUtils.ts
@@ -334,7 +334,8 @@ export function parseMarkdownContentTitle(
       contentTitle: toTextContentTitle(
         regularTitleMatch
           .groups!.title!.trim()
-          .replace(/\s*(?:\{#*[\w-]+\}|#+)$/, ''),
+          .replace(/(?:^|\s+)#+$/, '')
+          .replace(/\s*\{#*[\w-]+\}$/, ''),
       ).trim(),
     };
   }