diff --git a/src/services/formatting/rules.ts b/src/services/formatting/rules.ts
index 806dc6003f510..45d80841d1894 100644
--- a/src/services/formatting/rules.ts
+++ b/src/services/formatting/rules.ts
@@ -933,6 +933,13 @@ function isSemicolonDeletionContext(context: FormattingContext): boolean {
             || nextTokenKind === SyntaxKind.EndOfFileToken;
     }
 
+    if (
+        nextTokenKind === SyntaxKind.SemicolonToken &&
+        context.currentTokenSpan.kind === SyntaxKind.SemicolonToken
+    ) {
+        return true;
+    }
+
     if (
         nextTokenKind === SyntaxKind.SemicolonClassElement ||
         nextTokenKind === SyntaxKind.SemicolonToken
diff --git a/tests/cases/fourslash/formatRemoveSemicolons1.ts b/tests/cases/fourslash/formatRemoveSemicolons1.ts
index b80ecee7edb2d..39735fe0a8d93 100644
--- a/tests/cases/fourslash/formatRemoveSemicolons1.ts
+++ b/tests/cases/fourslash/formatRemoveSemicolons1.ts
@@ -51,7 +51,7 @@ class C {
     ["p"]
     zero: void
     ["one"] = {};
-    ["two"];
+    ["two"]
     ;
 }
 a;
@@ -59,7 +59,7 @@ a;
 b;
 (3)
 4;
-/ regex /;
+/ regex /
 ;
 [];
 /** blah */[0]
diff --git a/tests/cases/fourslash/formatRemoveSemicolons4.ts b/tests/cases/fourslash/formatRemoveSemicolons4.ts
new file mode 100644
index 0000000000000..299efa837a74c
--- /dev/null
+++ b/tests/cases/fourslash/formatRemoveSemicolons4.ts
@@ -0,0 +1,48 @@
+/// <reference path="fourslash.ts" />
+
+////declare const opt: number | undefined;
+////
+////const a = 1;
+////const b = 2;
+////;[1, 2, 3]
+////
+////const c = opt ? 1 : 2;
+////const d = opt ? 1 : 2;
+////;[1, 2, 3]
+////
+////const e = opt ?? 1;
+////const f = opt ?? 1;
+////;[1, 2, 3]
+////
+////type a = 1;
+////type b = 2;
+////;[1, 2, 3]
+////
+////type c = typeof opt extends 1 ? 1 : 2;
+////type d = typeof opt extends 1 ? 1 : 2;
+////;[1, 2, 3]
+
+format.setFormatOptions({ ...format.copyFormatOptions(), semicolons: ts.SemicolonPreference.Remove });
+format.document();
+verify.currentFileContentIs(
+`declare const opt: number | undefined
+
+const a = 1
+const b = 2
+;[1, 2, 3]
+
+const c = opt ? 1 : 2
+const d = opt ? 1 : 2
+;[1, 2, 3]
+
+const e = opt ?? 1
+const f = opt ?? 1
+;[1, 2, 3]
+
+type a = 1
+type b = 2
+;[1, 2, 3]
+
+type c = typeof opt extends 1 ? 1 : 2
+type d = typeof opt extends 1 ? 1 : 2
+;[1, 2, 3]`);