diff --git a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/Common.groovy b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/Common.groovy
index ff33fcd4d0..b8fca2e9c6 100644
--- a/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/Common.groovy
+++ b/spring-cloud-contract-spec/src/main/groovy/org/springframework/cloud/contract/spec/internal/Common.groovy
@@ -233,7 +233,7 @@ class Common {
 	}
 
 	void assertThatSidesMatch(OptionalProperty stubSide, Object testSide) {
-		assert testSide ==~ Pattern.compile(stubSide.optionalPattern())
+		assert testSide == null || testSide ==~ Pattern.compile(stubSide.optionalPattern())
 	}
 
 	void assertThatSidesMatch(Pattern pattern, String value) {
@@ -245,7 +245,7 @@ class Common {
 	}
 
 	void assertThatSidesMatch(MatchingStrategy firstSide, MatchingStrategy secondSide) {
-		if (firstSide.type == MatchingStrategy.Type.ABSENT && secondSide != MatchingStrategy.Type.ABSENT) {
+		if (firstSide.type == MatchingStrategy.Type.ABSENT && secondSide.type != MatchingStrategy.Type.ABSENT) {
 			throwAbsentError()
 		}
 	}
diff --git a/spring-cloud-contract-spec/src/test/groovy/org/springframework/cloud/contract/spec/internal/ContractSpec.groovy b/spring-cloud-contract-spec/src/test/groovy/org/springframework/cloud/contract/spec/internal/ContractSpec.groovy
index 4c36c70029..de2506e850 100644
--- a/spring-cloud-contract-spec/src/test/groovy/org/springframework/cloud/contract/spec/internal/ContractSpec.groovy
+++ b/spring-cloud-contract-spec/src/test/groovy/org/springframework/cloud/contract/spec/internal/ContractSpec.groovy
@@ -398,4 +398,28 @@ then:
 			assertThat(contract.request.bodyMatchers.hasMatchers()).isTrue()
 			assertThat(contract.response.bodyMatchers.hasMatchers()).isTrue()
 	}
+
+	def 'should work with optional and null value of a field'() {
+		given:
+			def contract = Contract.make {
+				description("Creating user")
+				name("Create user")
+				request {
+					method 'POST'
+					url '/api/user'
+					body(
+						address: $(consumer(optional(regex(alphaNumeric()))), producer(null)),
+						name: $(consumer(optional(regex(alphaNumeric()))), producer(''))
+					)
+					headers {
+						contentType(applicationJson())
+					}
+				}
+				response {
+					status 201
+				}
+			}
+		expect:
+			contract != null
+	}
 }
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
index aaa19436ad..b73707243c 100755
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockGroovyDslSpec.groovy
@@ -2713,6 +2713,47 @@ class WireMockGroovyDslSpec extends Specification implements WireMockStubVerifie
 
 	}
 
+	@Issue("#1257")
+	def "should work with null request element on the client side and optional stub entry"() {
+		given:
+			Contract contractDsl =  Contract.make {
+				description("Creating user")
+				name("Create user")
+				request {
+					method 'POST'
+					url '/api/user'
+					body(
+							address: $(consumer(optional(regex(alphaNumeric()))), producer(null)),
+							name: $(consumer(optional(regex(alphaNumeric()))), producer(''))
+					)
+					headers {
+						contentType(applicationJson())
+					}
+				}
+				response {
+					status 201
+				}
+			}
+		and:
+			String wireMockStub = new WireMockStubStrategy("Test",
+					new ContractMetadata(null, false, 0, null, contractDsl), contractDsl)
+					.toWireMockClientStub()
+
+		and:
+			int port = SocketUtils.findAvailableTcpPort()
+			WireMockServer server = new WireMockServer(config().port(port))
+			server.start()
+		and:
+			stubMappingIsValidWireMockStub(wireMockStub)
+			server.addStubMapping(WireMockStubMapping.buildFrom(wireMockStub))
+		when:
+			ResponseEntity<String> entity = callWithOptionalAndEmpty(port)
+		then:
+			entity.statusCodeValue == 201
+		cleanup:
+			server?.shutdown()
+	}
+
 	WireMockConfiguration config() {
 		return new WireMockConfiguration().extensions(responseTemplateTransformer())
 	}
@@ -2732,6 +2773,13 @@ class WireMockGroovyDslSpec extends Specification implements WireMockStubVerifie
 						.body("{\"foo\":\"bar\",\"baz\":5}"), String.class)
 	}
 
+	ResponseEntity<String> callWithOptionalAndEmpty(int port) {
+		return new TestRestTemplate().exchange(
+				RequestEntity.post(URI.create("http://localhost:" + port + "/api/user"))
+						.header("Content-Type", "application/json")
+						.body("{\"foo\":null,\"name\":\"\"}"), String.class)
+	}
+
 	ResponseEntity<byte[]> callBytes(int port, File request) {
 		return new TestRestTemplate().exchange(
 				RequestEntity.put(URI.create("http://localhost:" + port + "/1"))