diff --git a/tools/doc/html.mjs b/tools/doc/html.mjs
index 14461df589e23a..74bc82e66bcfd5 100644
--- a/tools/doc/html.mjs
+++ b/tools/doc/html.mjs
@@ -381,6 +381,7 @@ const DEPRECATION_HEADING_PATTERN = /^DEP\d+:/;
 export function buildToc({ filename, apilinks }) {
   return (tree, file) => {
     const idCounters = Object.create(null);
+    const legacyIdCounters = Object.create(null);
     let toc = '';
     let depth = 0;
 
@@ -399,6 +400,8 @@ export function buildToc({ filename, apilinks }) {
         node.children[0].position.start.offset,
         node.position.end.offset).trim();
       const id = getId(headingText, idCounters);
+      // Use previous ID generator to create alias
+      const legacyId = getLegacyId(`${realFilename}_${headingText}`, legacyIdCounters);
 
       const isDeprecationHeading =
         DEPRECATION_HEADING_PATTERN.test(headingText);
@@ -417,6 +420,9 @@ export function buildToc({ filename, apilinks }) {
       let anchor =
          `<span><a class="mark" href="#${id}" id="${id}">#</a></span>`;
 
+      // Add alias anchor to preserve old links
+      anchor += `<a class="legacy" id="${legacyId}"></a>`;
+
       if (realFilename === 'errors' && headingText.startsWith('ERR_')) {
         anchor +=
           `<span><a class="mark" href="#${headingText}" id="${headingText}">#</a></span>`;
@@ -446,6 +452,7 @@ export function buildToc({ filename, apilinks }) {
   };
 }
 
+// ID generator that mirrors Github's heading anchor parser
 const punctuation = /[^\w\- ]/g;
 function getId(text, idCounters) {
   text = text.toLowerCase()
@@ -458,6 +465,23 @@ function getId(text, idCounters) {
   return text;
 }
 
+// This ID generator is purely to generate aliases
+// so we can preserve old doc links
+const notAlphaNumerics = /[^a-z0-9]+/g;
+const edgeUnderscores = /^_+|_+$/g;
+const notAlphaStart = /^[^a-z]/;
+function getLegacyId(text, idCounters) {
+  text = text.toLowerCase()
+             .replace(notAlphaNumerics, '_')
+             .replace(edgeUnderscores, '')
+             .replace(notAlphaStart, '_$&');
+  if (idCounters[text] !== undefined) {
+    return `${text}_${++idCounters[text]}`;
+  }
+  idCounters[text] = 0;
+  return text;
+}
+
 function altDocs(filename, docCreated, versions) {
   const [, docCreatedMajor, docCreatedMinor] = docCreated.map(Number);
   const host = 'https://nodejs.org';