diff --git a/packages/playwright-test/src/matchers/matchers.ts b/packages/playwright-test/src/matchers/matchers.ts
index 3d39c390fb0da..b9477377e340c 100644
--- a/packages/playwright-test/src/matchers/matchers.ts
+++ b/packages/playwright-test/src/matchers/matchers.ts
@@ -358,5 +358,5 @@ export async function toPass(
     `- ${timeoutMessage}`,
   ].join('\n') : timeoutMessage;
 
-  return { message, pass: false };
+  return { message, pass: isNot ? true : false };
 }
diff --git a/tests/playwright-test/expect-to-pass.spec.ts b/tests/playwright-test/expect-to-pass.spec.ts
index d76cf094c1f61..82f630843805e 100644
--- a/tests/playwright-test/expect-to-pass.spec.ts
+++ b/tests/playwright-test/expect-to-pass.spec.ts
@@ -166,4 +166,17 @@ test('should work with soft', async ({ runInlineTest }) => {
   expect(stripAnsi(result.output)).toContain('Received: 2');
   expect(result.exitCode).toBe(1);
   expect(result.failed).toBe(1);
-});
\ No newline at end of file
+});
+
+test('should not accept TimeoutError', async ({ runInlineTest }) => {
+  const result = await runInlineTest({
+    'a.spec.ts': `
+      const { test } = pwt;
+      test('should fail', async () => {
+        await test.expect(() => {}).not.toPass({ timeout: 1 });
+      });
+    `
+  });
+  expect(result.exitCode).toBe(1);
+  expect(result.failed).toBe(1);
+});