diff --git a/packages/expect/src/types.ts b/packages/expect/src/types.ts
index 17eac43c1..fd0d2a58b 100644
--- a/packages/expect/src/types.ts
+++ b/packages/expect/src/types.ts
@@ -186,13 +186,13 @@ export interface AsymmetricMatchersContaining extends CustomMatcher {
   closeTo: (expected: number, precision?: number) => any
 }
 
+type WithAsymmetricMatcher<T> = T | AsymmetricMatcher<unknown>
+
 export type DeeplyAllowMatchers<T> = T extends Array<infer Element>
-  ? (DeeplyAllowMatchers<Element> | Element)[]
+  ? WithAsymmetricMatcher<T> | DeeplyAllowMatchers<Element>[]
   : T extends object
-    ? {
-        [K in keyof T]: DeeplyAllowMatchers<T[K]> | AsymmetricMatcher<unknown>
-      }
-    : T
+    ? WithAsymmetricMatcher<T> | { [K in keyof T]: DeeplyAllowMatchers<T[K]> }
+    : WithAsymmetricMatcher<T>
 
 export interface JestAssertion<T = any> extends jest.Matchers<void, T>, CustomMatcher {
   /**
diff --git a/test/core/test/expect.test-d.ts b/test/core/test/expect.test-d.ts
index 1add65213..20e480bb9 100644
--- a/test/core/test/expect.test-d.ts
+++ b/test/core/test/expect.test-d.ts
@@ -111,4 +111,12 @@ test('expect.* allows asymmetrict mattchers with different types', () => {
   // https://github.com/DefinitelyTyped/DefinitelyTyped/pull/62831/files#diff-ff7b882e4a29e7fe0e348a6bdf8b11774d606eaa221009b166b01389576d921fR1237
   expect({ list: [1, 2, 3] }).toMatchObject({ list: expect.any(Array) })
   expect({ list: [1, 2, 3] }).toMatchObject<{ list: number[] }>({ list: expect.any(Array) })
+
+  // expect<T>
+  // https://github.com/vitest-dev/vitest/issues/8081
+  function expectMany<T>(value: ({ enabled: false } | { enabled: true; data: T })) {
+    expect(value).toEqual(value)
+    expect(value).toMatchObject(value)
+  }
+  expectMany({ enabled: true, data: 'ok' })
 })