diff --git a/src/compat/predicate/isMatch.spec.ts b/src/compat/predicate/isMatch.spec.ts
index 073ca4d79..58213df20 100644
--- a/src/compat/predicate/isMatch.spec.ts
+++ b/src/compat/predicate/isMatch.spec.ts
@@ -316,6 +316,24 @@ describe('isMatch', () => {
     delete numberProto.b;
   });
 
+  it('should return `false` when target is primitive and source is object with undefined values (Issue #1399)', () => {
+    // eslint-disable-next-line @typescript-eslint/ban-ts-comment
+    // @ts-expect-error
+    expect(isMatch('bar', { anyKey: undefined })).toBe(false);
+    // eslint-disable-next-line @typescript-eslint/ban-ts-comment
+    // @ts-expect-error
+    expect(isMatch(123, { anyKey: undefined })).toBe(false);
+    // eslint-disable-next-line @typescript-eslint/ban-ts-comment
+    // @ts-expect-error
+    expect(isMatch(true, { anyKey: undefined })).toBe(false);
+  });
+
+  it('should return `false` when target is primitive and source is empty object nested (Issue #1399)', () => {
+    expect(isMatch({ value: 'bar' }, { value: {} })).toBe(false);
+    expect(isMatch({ value: 123 }, { value: {} })).toBe(false);
+    expect(isMatch({ value: true }, { value: {} })).toBe(false);
+  });
+
   it(`should return \`false\` when \`object\` is nullish`, () => {
     // eslint-disable-next-line no-sparse-arrays
     const values = [, null, undefined];
diff --git a/src/compat/predicate/isMatchWith.ts b/src/compat/predicate/isMatchWith.ts
index ddcaabdfe..823060a58 100644
--- a/src/compat/predicate/isMatchWith.ts
+++ b/src/compat/predicate/isMatchWith.ts
@@ -206,7 +206,14 @@ function isObjectMatch(
   const keys = Object.keys(source as any);
 
   if (target == null) {
-    return keys.length === 0;
+    if (stack && stack.size > 0 && !isObject(target)) {
+      return false;
+    }
+    return true;
+  }
+
+  if (!isObject(target)) {
+    return false;
   }
 
   if (keys.length === 0) {