diff --git a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/Input.java b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/Input.java
index 92a2077f0c..b3dcc3dc05 100644
--- a/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/Input.java
+++ b/specs/spring-cloud-contract-spec-java/src/main/java/org/springframework/cloud/contract/spec/internal/Input.java
@@ -294,8 +294,6 @@ public class Input extends Common implements RegexCreatingProperty<ClientDslProp
 	/**
 	 * The stub matchers part of the contract.
 	 * @param consumer function to manipulate the message headers
-	 * @deprecated Deprecated in favor of bodyMatchers to support other future
-	 * bodyMatchers too
 	 */
 	public void bodyMatchers(Consumer<BodyMatchers> consumer) {
 		this.bodyMatchers = new BodyMatchers();
@@ -315,8 +313,6 @@ public class Input extends Common implements RegexCreatingProperty<ClientDslProp
 	/**
 	 * The stub matchers part of the contract.
 	 * @param consumer function to manipulate the message headers
-	 * @deprecated Deprecated in favor of bodyMatchers to support other future
-	 * bodyMatchers too
 	 */
 	public void bodyMatchers(@DelegatesTo(BodyMatchers.class) Closure consumer) {
 		this.bodyMatchers = new BodyMatchers();
diff --git a/spring-cloud-contract-verifier/src/main/java/org/springframework/cloud/contract/verifier/converter/YamlToContracts.java b/spring-cloud-contract-verifier/src/main/java/org/springframework/cloud/contract/verifier/converter/YamlToContracts.java
index 3ffe7df1b3..c3bbad2707 100644
--- a/spring-cloud-contract-verifier/src/main/java/org/springframework/cloud/contract/verifier/converter/YamlToContracts.java
+++ b/spring-cloud-contract-verifier/src/main/java/org/springframework/cloud/contract/verifier/converter/YamlToContracts.java
@@ -245,7 +245,7 @@ class YamlToContracts {
 								serverValue(value, matcher)));
 					}
 				});
-				if (matchers != null) {
+				if (matchers.isEmpty()) {
 					headers.header(key, value);
 				}
 			}));
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockRequestStubStrategySpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockRequestStubStrategySpec.groovy
new file mode 100644
index 0000000000..04e4b4eb8e
--- /dev/null
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockRequestStubStrategySpec.groovy
@@ -0,0 +1,76 @@
+/*
+ * Copyright 2013-2020 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.cloud.contract.verifier.dsl.wiremock
+
+
+import org.springframework.cloud.contract.spec.Contract
+import org.springframework.cloud.contract.verifier.converter.YamlContractConverter
+import org.springframework.cloud.contract.verifier.file.SingleContractMetadata
+import org.springframework.cloud.contract.verifier.util.ContentType
+import spock.lang.Issue
+import spock.lang.Specification
+
+class WireMockRequestStubStrategySpec extends Specification {
+
+	@Issue("#1666")
+	def "should match header regex from request YAML"() {
+		given:
+			String yaml = """
+name: upload-file
+request:
+  method: POST
+  url: /user/upload-file
+  headers:
+    Content-Type: multipart/form-data;boundary=AaB03x
+  multipart:
+    params:
+      name: "fileName.md"
+    named:
+      - paramName: "file"
+        fileName: "fileName.md"
+        fileContent: "file content"
+  matchers:
+    headers:
+      - key: Content-Type
+        regex: "multipart/form\\\\-data.*"
+    multipart:
+      params:
+        - key: name
+          regex: ".+"
+      named:
+        - paramName: "file"
+          fileName:
+            predefined: non_empty
+          fileContent:
+            predefined: non_empty
+response:
+  status: 200
+  body:
+    foo: bar
+"""
+			File tmp = File.createTempFile("foo" + System.currentTimeMillis(), ".yml")
+			tmp.write(yaml)
+			Contract contract = new YamlContractConverter().convertFrom(tmp).first()
+		when:
+			SingleContractMetadata metadata = Stub()
+			metadata.evaluatedOutputStubContentType >> ContentType.JSON
+			def subject = new WireMockRequestStubStrategy(contract, metadata)
+			def content = subject.buildClientRequestContent()
+		then:
+			content.getHeaders().get("Content-Type").getValuePattern().getValue() != "multipart/form-data;boundary=AaB03x"
+	}
+}
diff --git a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockResponseStubStrategySpec.groovy b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockResponseStubStrategySpec.groovy
index 1492e62527..3bad520dbf 100644
--- a/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockResponseStubStrategySpec.groovy
+++ b/spring-cloud-contract-verifier/src/test/groovy/org/springframework/cloud/contract/verifier/dsl/wiremock/WireMockResponseStubStrategySpec.groovy
@@ -16,16 +16,16 @@
 
 package org.springframework.cloud.contract.verifier.dsl.wiremock
 
-import java.util.function.Function
-
 import groovy.json.JsonSlurper
-import spock.lang.Issue
-import spock.lang.Specification
-
 import org.springframework.cloud.contract.spec.Contract
+import org.springframework.cloud.contract.verifier.converter.YamlContractConverter
 import org.springframework.cloud.contract.verifier.file.SingleContractMetadata
 import org.springframework.cloud.contract.verifier.util.ContentType
 import org.springframework.cloud.contract.verifier.util.MapConverter
+import spock.lang.Issue
+import spock.lang.Specification
+
+import java.util.function.Function
 
 class WireMockResponseStubStrategySpec extends Specification {