diff --git a/src/test/suite/integration/toc.test.ts b/src/test/suite/integration/toc.test.ts
index 506bae84..cdd7cfa3 100644
--- a/src/test/suite/integration/toc.test.ts
+++ b/src/test/suite/integration/toc.test.ts
@@ -206,6 +206,59 @@ suite("TOC.", () => {
 
     });
 
+    test("Ordered list (list markers larger than 9)", async () => {
+        await updateConfiguration({ config: [["markdown.extension.toc.orderedList", true]] });
+        await testCommand('markdown.extension.toc.create',
+            [
+                '# H1',
+                '# H2',
+                '# H3',
+                '# H4',
+                '# H5',
+                '# H6',
+                '# H7',
+                '# H8',
+                '# H9',
+                '# H10',
+                '## H11',
+                '### H12',
+                '',
+                ''
+            ],
+            new Selection(13, 0, 13, 0),
+            [
+                '# H1',
+                '# H2',
+                '# H3',
+                '# H4',
+                '# H5',
+                '# H6',
+                '# H7',
+                '# H8',
+                '# H9',
+                '# H10',
+                '## H11',
+                '### H12',
+                '',
+                '1. [H1](#h1)',
+                '2. [H2](#h2)',
+                '3. [H3](#h3)',
+                '4. [H4](#h4)',
+                '5. [H5](#h5)',
+                '6. [H6](#h6)',
+                '7. [H7](#h7)',
+                '8. [H8](#h8)',
+                '9. [H9](#h9)',
+                '10. [H10](#h10)',
+                '    1. [H11](#h11)',
+                '       1. [H12](#h12)',
+                ''
+            ],
+            new Selection(25, 0, 25, 0)
+        );
+        await resetConfiguration();
+    });
+
     test("Setext headings", () => {
         return testCommand('markdown.extension.toc.create',
             [
diff --git a/src/toc.ts b/src/toc.ts
index 6c090f11..368c48ea 100644
--- a/src/toc.ts
+++ b/src/toc.ts
@@ -263,19 +263,28 @@ async function generateTocText(doc: TextDocument): Promise<string> {
 
     // The actual level range of a document can be smaller than settings. So we need to calculate the real start level.
     const startDepth = Math.max(tocConfig.startDepth, Math.min(...tocEntries.map(h => h.level)));
-    const order: number[] = new Array(tocConfig.endDepth - startDepth + 1).fill(0); // Used for ordered list
+    // Order counter for each heading level (from startDepth to endDepth), used only for ordered list
+    const orderCounter: number[] = new Array(tocConfig.endDepth - startDepth + 1).fill(0);
 
     tocEntries.forEach(entry => {
         const relativeLevel = entry.level - startDepth;
+        const currHeadingOrder = ++orderCounter[relativeLevel];
+        let indentationFix = '';
+        if (tocConfig.orderedList) {
+            const shift = orderCounter.slice(0, relativeLevel).map(c => String(c).length - 1).reduce((a, b) => a + b, 0);
+            indentationFix = ' '.repeat(shift);
+        }
 
         const row = [
-            docConfig.tab.repeat(relativeLevel),
-            (tocConfig.orderedList ? (orderedListMarkerIsOne ? '1' : ++order[relativeLevel]) + '.' : tocConfig.listMarker) + ' ',
+            docConfig.tab.repeat(relativeLevel) + indentationFix,
+            (tocConfig.orderedList ? (orderedListMarkerIsOne ? '1' : currHeadingOrder) + '.' : tocConfig.listMarker) + ' ',
             tocConfig.plaintext ? entry.visibleText : `[${entry.visibleText}](#${entry.slug})`
         ];
         toc.push(row.join(''));
+
+        // Reset order counter for its sub-headings
         if (tocConfig.orderedList) {
-            order.fill(0, relativeLevel + 1);
+            orderCounter.fill(0, relativeLevel + 1);
         }
     });
     while (/^[ \t]/.test(toc[0])) {