diff --git a/pkg/engine/variables/operator/anyin.go b/pkg/engine/variables/operator/anyin.go
index cc6ad419c1..cf667e5283 100644
--- a/pkg/engine/variables/operator/anyin.go
+++ b/pkg/engine/variables/operator/anyin.go
@@ -63,7 +63,7 @@ func anyKeyExistsInArray(key string, value interface{}, log logr.Logger) (invali
 
 	case []interface{}:
 		for _, val := range valuesAvailable {
-			if wildcard.Match(fmt.Sprint(val), key) {
+			if wildcard.Match(fmt.Sprint(val), key) || wildcard.Match(key, fmt.Sprint(val)) {
 				return false, true
 			}
 		}
diff --git a/pkg/engine/variables/operator/in.go b/pkg/engine/variables/operator/in.go
index 2eaaeb88fe..763d3300b4 100644
--- a/pkg/engine/variables/operator/in.go
+++ b/pkg/engine/variables/operator/in.go
@@ -63,7 +63,7 @@ func keyExistsInArray(key string, value interface{}, log logr.Logger) (invalidTy
 
 	case []interface{}:
 		for _, val := range valuesAvailable {
-			if wildcard.Match(fmt.Sprint(val), key) {
+			if wildcard.Match(fmt.Sprint(val), key) || wildcard.Match(key, fmt.Sprint(val)) {
 				return false, true
 			}
 		}
diff --git a/test/cli/test/context-entries/kyverno-test.yaml b/test/cli/test/context-entries/kyverno-test.yaml
index 1df2ecd642..a2463de519 100644
--- a/test/cli/test/context-entries/kyverno-test.yaml
+++ b/test/cli/test/context-entries/kyverno-test.yaml
@@ -44,3 +44,8 @@ results:
     resource: example
     kind: Pod
     result: pass
+  - policy: example
+    rule:  wildcard-match
+    resource: example
+    kind: Pod
+    result: pass
diff --git a/test/cli/test/context-entries/policies.yaml b/test/cli/test/context-entries/policies.yaml
index 77062e3c85..6c95d44497 100644
--- a/test/cli/test/context-entries/policies.yaml
+++ b/test/cli/test/context-entries/policies.yaml
@@ -146,3 +146,20 @@ spec:
             - key: "{{ to_string(obj.notName) }}"
               operator: NotEquals
               value: 'null'
+  - name: wildcard-match
+    context:
+    - name: obj
+      variable:
+        value: 
+         - A=ATest
+         - B=BTest
+    match:
+      resources:
+        kinds:
+        - Pod
+    validate:
+      deny:
+        conditions:
+          - key: "A=*"
+            operator: AnyNotIn
+            value: "{{ obj }}"