diff --git a/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelector.java b/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelector.java
index 7994023f95..c99ce1bdbc 100644
--- a/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelector.java
+++ b/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelector.java
@@ -233,8 +233,8 @@ class StubRunnerIntegrationMessageSelector implements MessageSelector {
 			Object value = it.getClientValue();
 			Object valueInHeader = headers.get(name);
 			boolean matches;
-			if (value instanceof RegexProperty) {
-				Pattern pattern = ((RegexProperty) value).getPattern();
+			if (value instanceof RegexProperty || value instanceof Pattern) {
+				Pattern pattern = new RegexProperty(value).getPattern();
 				matches = pattern.matcher(valueInHeader.toString()).matches();
 			}
 			else {
diff --git a/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelector.java b/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelector.java
index 75f9572441..73c4be3961 100644
--- a/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelector.java
+++ b/spring-cloud-contract-stub-runner/src/main/java/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelector.java
@@ -234,8 +234,8 @@ class StubRunnerStreamMessageSelector implements MessageSelector {
 			Object value = it.getClientValue();
 			Object valueInHeader = headers.get(name);
 			boolean matches;
-			if (value instanceof RegexProperty) {
-				Pattern pattern = ((RegexProperty) value).getPattern();
+			if (value instanceof RegexProperty || value instanceof Pattern) {
+				Pattern pattern = new RegexProperty(value).getPattern();
 				matches = pattern.matcher(valueInHeader.toString()).matches();
 			}
 			else {
diff --git a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelectorSpec.groovy b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelectorSpec.groovy
index 9d27fd1390..ba0a1371dc 100644
--- a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelectorSpec.groovy
+++ b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/integration/StubRunnerIntegrationMessageSelectorSpec.groovy
@@ -16,6 +16,7 @@
 
 package org.springframework.cloud.contract.stubrunner.messaging.integration
 
+import spock.lang.Issue
 import spock.lang.Specification
 
 import org.springframework.cloud.contract.spec.Contract
@@ -181,7 +182,8 @@ class StubRunnerIntegrationMessageSelectorSpec extends Specification {
 				}
 			}
 		and:
-			StubRunnerIntegrationMessageSelector predicate = new StubRunnerIntegrationMessageSelector(dsl)
+			StubRunnerIntegrationMessageSelector predicate = new StubRunnerIntegrationMessageSelector(
+					dsl)
 			message.headers >> [
 					foo: 123
 			]
@@ -191,4 +193,29 @@ class StubRunnerIntegrationMessageSelectorSpec extends Specification {
 		expect:
 			predicate.accept(message)
 	}
+
+	@Issue("1382")
+	def "should return true if header matches regex"() {
+		given:
+			Contract dsl = Contract.make {
+				input {
+					messageFrom "foo"
+					messageHeaders {
+						header("foo", $(anyUuid()))
+					}
+					messageBody(foo: 123)
+				}
+			}
+		and:
+			StubRunnerIntegrationMessageSelector predicate = new StubRunnerIntegrationMessageSelector(
+					dsl)
+			message.headers >> [
+					foo: "fbcc2ed3-dbac-47e7-9a4b-c2d55709792c"
+			]
+			message.payload >> [
+					foo: 123
+			]
+		expect:
+			predicate.accept(message)
+	}
 }
diff --git a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelectorSpec.groovy b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelectorSpec.groovy
index e770cb1f84..8a969773d1 100644
--- a/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelectorSpec.groovy
+++ b/spring-cloud-contract-stub-runner/src/test/groovy/org/springframework/cloud/contract/stubrunner/messaging/stream/StubRunnerStreamMessageSelectorSpec.groovy
@@ -16,6 +16,7 @@
 
 package org.springframework.cloud.contract.stubrunner.messaging.stream
 
+import spock.lang.Issue
 import spock.lang.Specification
 
 import org.springframework.cloud.contract.spec.Contract
@@ -210,7 +211,8 @@ class StubRunnerStreamMessageSelectorSpec extends Specification {
 				}
 			}
 		and:
-			StubRunnerStreamMessageSelector predicate = new StubRunnerStreamMessageSelector(dsl)
+			StubRunnerStreamMessageSelector predicate = new StubRunnerStreamMessageSelector(
+					dsl)
 			message.headers >> [
 					foo: 123
 			]
@@ -220,4 +222,29 @@ class StubRunnerStreamMessageSelectorSpec extends Specification {
 		expect:
 			predicate.accept(message)
 	}
+
+	@Issue("1382")
+	def "should return true if header matches regex"() {
+		given:
+			Contract dsl = Contract.make {
+				input {
+					messageFrom "foo"
+					messageHeaders {
+						header("foo", $(anyUuid()))
+					}
+					messageBody(foo: 123)
+				}
+			}
+		and:
+			StubRunnerStreamMessageSelector predicate = new StubRunnerStreamMessageSelector(
+					dsl)
+			message.headers >> [
+					foo: "fbcc2ed3-dbac-47e7-9a4b-c2d55709792c"
+			]
+			message.payload >> [
+					foo: 123
+			]
+		expect:
+			predicate.accept(message)
+	}
 }