diff --git a/test/integration/apiserver/admissionwebhook/match_conditions_test.go b/test/integration/apiserver/admissionwebhook/match_conditions_test.go
index cdbc17ead4c..b642eeb6585 100644
--- a/test/integration/apiserver/admissionwebhook/match_conditions_test.go
+++ b/test/integration/apiserver/admissionwebhook/match_conditions_test.go
@@ -727,6 +727,197 @@ func TestMatchConditions_validation(t *testing.T) {
 	}
 }
 
+func TestFeatureGateEnablement(t *testing.T) {
+	testcases := []struct {
+		name                                  string
+		matchConditionsFeatureGateInitiaState string
+		matchConditions                       []admissionregistrationv1.MatchCondition
+		expectMatchConditionsPreSwitch        bool
+		expectMatchConditionsPostSwitch       bool
+	}{
+		{
+			name:                                  "start with match conditions enabled - no match conditions",
+			matchConditionsFeatureGateInitiaState: "enabled",
+			expectMatchConditionsPreSwitch:        false,
+			expectMatchConditionsPostSwitch:       false,
+		},
+		{
+			name:                                  "start with match conditions enabled - with match conditions",
+			matchConditionsFeatureGateInitiaState: "enabled",
+			matchConditions: []admissionregistrationv1.MatchCondition{{
+				Name:       "test-expression",
+				Expression: "true",
+			}},
+			expectMatchConditionsPreSwitch:  true,
+			expectMatchConditionsPostSwitch: true,
+		},
+		{
+			name:                                  "start with match conditions disabled - no match conditions",
+			matchConditionsFeatureGateInitiaState: "disabled",
+			expectMatchConditionsPreSwitch:        false,
+			expectMatchConditionsPostSwitch:       false,
+		},
+		{
+			name:                                  "start with match conditions disabled - with match conditions",
+			matchConditionsFeatureGateInitiaState: "disabled",
+			matchConditions: []admissionregistrationv1.MatchCondition{{
+				Name:       "test-expression",
+				Expression: "true",
+			}},
+			expectMatchConditionsPreSwitch:  false,
+			expectMatchConditionsPostSwitch: false,
+		},
+	}
+
+	server := apiservertesting.StartTestServerOrDie(t, nil, []string{
+		"--disable-admission-plugins=ServiceAccount",
+	}, framework.SharedEtcd())
+	defer server.TearDownFn()
+
+	endpoint := "https://localhost:1234/server"
+	clientConfig := admissionregistrationv1.WebhookClientConfig{
+		URL:      &endpoint,
+		CABundle: localhostCert,
+	}
+
+	rules := []admissionregistrationv1.RuleWithOperations{{
+		Operations: []admissionregistrationv1.OperationType{admissionregistrationv1.Create},
+		Rule: admissionregistrationv1.Rule{
+			APIGroups:   []string{""},
+			APIVersions: []string{"v1"},
+			Resources:   []string{"pods"},
+		},
+	}}
+	versions := []string{"v1"}
+
+	client := clientset.NewForConfigOrDie(server.ClientConfig)
+
+	for _, testcase := range testcases {
+		t.Run(testcase.name, func(t *testing.T) {
+			if testcase.matchConditionsFeatureGateInitiaState == "enabled" {
+				defer featuregatetesting.SetFeatureGateDuringTest(t, utilfeature.DefaultFeatureGate, genericfeatures.AdmissionWebhookMatchConditions, true)()
+			}
+
+			validatingwebhook := &admissionregistrationv1.ValidatingWebhookConfiguration{
+				ObjectMeta: metav1.ObjectMeta{
+					Name: "validating-webhook.integration.test",
+				},
+				Webhooks: []admissionregistrationv1.ValidatingWebhook{
+					{
+						Name:                    "admission.integration.test",
+						Rules:                   rules,
+						ClientConfig:            clientConfig,
+						SideEffects:             &noSideEffects,
+						AdmissionReviewVersions: versions,
+						MatchConditions:         testcase.matchConditions,
+					},
+				},
+			}
+
+			mutatingWebhook := &admissionregistrationv1.MutatingWebhookConfiguration{
+				ObjectMeta: metav1.ObjectMeta{
+					Name: "mutating-webhook.integration.test",
+				},
+				Webhooks: []admissionregistrationv1.MutatingWebhook{
+					{
+						Name:                    "admission.integration.test",
+						Rules:                   rules,
+						ClientConfig:            clientConfig,
+						SideEffects:             &noSideEffects,
+						AdmissionReviewVersions: versions,
+						MatchConditions:         testcase.matchConditions,
+					},
+				},
+			}
+
+			// Create the validating webhook
+			_, err := client.AdmissionregistrationV1().ValidatingWebhookConfigurations().Create(
+				context.Background(), validatingwebhook, metav1.CreateOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error creating validating webhook: %v", err)
+			}
+			t.Cleanup(func() {
+				// Make sure to cleanup the validating webhook before running the next test case
+				err := client.AdmissionregistrationV1().ValidatingWebhookConfigurations().Delete(
+					context.Background(), validatingwebhook.Name, metav1.DeleteOptions{},
+				)
+				if err != nil {
+					t.Fatalf("Unexpected error deleting validating webhook: %v", err)
+				}
+			})
+
+			// Create the mutating webhook
+			_, err = client.AdmissionregistrationV1().MutatingWebhookConfigurations().Create(
+				context.Background(), mutatingWebhook, metav1.CreateOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error creating mutating webhook: %v", err)
+			}
+			t.Cleanup(func() {
+				// Make sure to cleanup the mutating webhook before running the next test case
+				err := client.AdmissionregistrationV1().MutatingWebhookConfigurations().Delete(
+					context.Background(), mutatingWebhook.Name, metav1.DeleteOptions{},
+				)
+				if err != nil {
+					t.Fatalf("Unexpected error deleting mutating webhook: %v", err)
+				}
+			})
+
+			// Assert the validating webhook match conditions field - pre switch
+			validatingWebhookConfig, err := client.AdmissionregistrationV1().ValidatingWebhookConfigurations().Get(
+				context.Background(), validatingwebhook.Name, metav1.GetOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error getting validating webhook: %v", err)
+			}
+			if testcase.expectMatchConditionsPreSwitch && validatingWebhookConfig.Webhooks[0].MatchConditions == nil {
+				t.Fatal("Expected match conditions to be present in the validating webhook pre switch; got: nil")
+			}
+
+			// Assert the mutating webhook match conditions field - pre switch
+			mutatingWebhookConfig, err := client.AdmissionregistrationV1().MutatingWebhookConfigurations().Get(
+				context.Background(), mutatingWebhook.Name, metav1.GetOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error getting mutating webhook: %v", err)
+			}
+			if testcase.expectMatchConditionsPreSwitch && mutatingWebhookConfig.Webhooks[0].MatchConditions == nil {
+				t.Fatal("Expected match conditions to be present in the mutating webhook pre switch; got: nil")
+			}
+
+			// Switch the featureGate state
+			if testcase.matchConditionsFeatureGateInitiaState == "enabled" {
+				defer featuregatetesting.SetFeatureGateDuringTest(t, utilfeature.DefaultFeatureGate, genericfeatures.AdmissionWebhookMatchConditions, false)()
+			} else {
+				defer featuregatetesting.SetFeatureGateDuringTest(t, utilfeature.DefaultFeatureGate, genericfeatures.AdmissionWebhookMatchConditions, true)()
+			}
+
+			// Assert the validating webhook match conditions field - post switch
+			validatingWebhookConfig, err = client.AdmissionregistrationV1().ValidatingWebhookConfigurations().Get(
+				context.Background(), validatingwebhook.Name, metav1.GetOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error getting validating webhook: %v", err)
+			}
+			if testcase.expectMatchConditionsPostSwitch && validatingWebhookConfig.Webhooks[0].MatchConditions == nil {
+				t.Fatal("Expected match conditions to be present in the validating webhook post switch; got: nil")
+			}
+
+			// Assert the mutating webhook match conditions field - post switch
+			mutatingWebhookConfig, err = client.AdmissionregistrationV1().MutatingWebhookConfigurations().Get(
+				context.Background(), mutatingWebhook.Name, metav1.GetOptions{},
+			)
+			if err != nil {
+				t.Fatalf("Unexpected error getting mutating webhook: %v", err)
+			}
+			if testcase.expectMatchConditionsPostSwitch && mutatingWebhookConfig.Webhooks[0].MatchConditions == nil {
+				t.Fatal("Expected match conditions to be present in the mutating webhook post switch; got: nil")
+			}
+		})
+	}
+}
+
 func matchConditionsTestPod(name, ns string) *corev1.Pod {
 	return &corev1.Pod{
 		ObjectMeta: metav1.ObjectMeta{