diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockRestServiceServer.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockRestServiceServer.java
index 6587602cba..bbb5f36d9a 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockRestServiceServer.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockRestServiceServer.java
@@ -16,6 +16,8 @@
 
 package org.springframework.cloud.contract.wiremock;
 
+import org.hamcrest.BaseMatcher;
+import org.hamcrest.Description;
 import org.springframework.core.io.Resource;
 import org.springframework.core.io.support.PathMatchingResourcePatternResolver;
 import org.springframework.http.HttpHeaders;
@@ -37,9 +39,11 @@ import java.util.List;
 
 import com.github.tomakehurst.wiremock.common.Json;
 import com.github.tomakehurst.wiremock.http.HttpHeader;
+import com.github.tomakehurst.wiremock.http.MultiValue;
 import com.github.tomakehurst.wiremock.http.ResponseDefinition;
 import com.github.tomakehurst.wiremock.matching.MultiValuePattern;
 import com.github.tomakehurst.wiremock.matching.RequestPattern;
+import com.github.tomakehurst.wiremock.stubbing.SortedConcurrentMappingSet;
 import com.github.tomakehurst.wiremock.stubbing.StubMapping;
 
 import static org.springframework.test.web.client.match.MockRestRequestMatchers.header;
@@ -147,14 +151,12 @@ public class WireMockRestServiceServer {
 	 */
 	public MockRestServiceServer build() {
 		MockRestServiceServer server = this.builder.build();
+		SortedConcurrentMappingSet mappings = new SortedConcurrentMappingSet();
 		for (String location : this.locations) {
 			try {
 				for (Resource resource : this.resolver.getResources(pattern(location))) {
 					StubMapping mapping = mapping(resource);
-					ResponseActions expect = server
-							.expect(requestTo(request(mapping.getRequest())));
-					requestHeaders(expect, mapping.getRequest());
-					expect.andRespond(response(mapping.getResponse()));
+					mappings.add(mapping);
 				}
 			}
 			catch (IOException e) {
@@ -162,6 +164,12 @@ public class WireMockRestServiceServer {
 						e);
 			}
 		}
+		for (StubMapping mapping : mappings) {
+			ResponseActions expect = server
+					.expect(requestTo(request(mapping.getRequest())));
+			requestHeaders(expect, mapping.getRequest());
+			expect.andRespond(response(mapping.getResponse()));
+		}
 		return server;
 	}
 
@@ -194,10 +202,22 @@ public class WireMockRestServiceServer {
 		if (request.getHeaders() != null) {
 			for (final String header : request.getHeaders().keySet()) {
 				final MultiValuePattern pattern = request.getHeaders().get(header);
-				// TODO: match the headers
-				if ("equalTo".equals(pattern.getName())) {
-					expect.andExpect(header(header, pattern.getExpected()));
-				}
+				expect.andExpect(header(header, new BaseMatcher<String>() {
+
+					@Override
+					public boolean matches(Object item) {
+						return pattern.match(
+								new MultiValue(header, Arrays.asList((String) item)))
+								.isExactMatch();
+					}
+
+					@Override
+					public void describeTo(Description description) {
+						description
+								.appendText("should match header: " + header + " with ")
+								.appendText(pattern.getExpected());
+					}
+				}));
 			}
 		}
 	}
diff --git a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/WiremockMockServerApplicationTests.java b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/WiremockMockServerApplicationTests.java
index 40c2f0c625..59f0d0e686 100644
--- a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/WiremockMockServerApplicationTests.java
+++ b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/WiremockMockServerApplicationTests.java
@@ -67,14 +67,36 @@ public class WiremockMockServerApplicationTests {
 	@Test
 	public void postWithHeader() throws Exception {
 		WireMockRestServiceServer.with(this.restTemplate) //
-				.baseUrl("http://example.org") //
-				.stubs("classpath:/mappings/*.json").ignoreExpectOrder(true).build();
+				.baseUrl("http://example.org") // order matters...
+				.stubs("classpath:/mappings/poster.json", "classpath:/mappings/accept.json").ignoreExpectOrder(true).build();
 		assertThat(this.restTemplate
 				.exchange(RequestEntity.post(new URI("http://example.org/poster"))
 						.accept(MediaType.TEXT_PLAIN).build(), String.class)
 				.getBody()).isEqualTo("Accepted World");
 	}
 
+	@Test
+	public void postWithHeaderContains() throws Exception {
+		WireMockRestServiceServer.with(this.restTemplate) //
+				.baseUrl("http://example.org") // order matters...
+				.stubs("classpath:/mappings/poster.json", "classpath:/mappings/header-contains.json").ignoreExpectOrder(true).build();
+		assertThat(this.restTemplate
+				.exchange(RequestEntity.post(new URI("http://example.org/poster"))
+						.accept(MediaType.valueOf("application/v.foo")).build(), String.class)
+				.getBody()).isEqualTo("Foo World");
+	}
+
+	@Test
+	public void postWithHeaderMatches() throws Exception {
+		WireMockRestServiceServer.with(this.restTemplate) //
+				.baseUrl("http://example.org") // order matters...
+				.stubs("classpath:/mappings/poster.json", "classpath:/mappings/header-matches.json").ignoreExpectOrder(true).build();
+		assertThat(this.restTemplate
+				.exchange(RequestEntity.post(new URI("http://example.org/poster"))
+						.accept(MediaType.valueOf("application/v.bar")).build(), String.class)
+				.getBody()).isEqualTo("Bar World");
+	}
+
 	@Test
 	public void simpleGetWithAllStubs() throws Exception {
 		WireMockRestServiceServer.with(this.restTemplate) //
diff --git a/spring-cloud-contract-wiremock/src/test/resources/mappings/header-contains.json b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-contains.json
new file mode 100644
index 0000000000..b862f326bc
--- /dev/null
+++ b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-contains.json
@@ -0,0 +1,11 @@
+{
+  "request" : {
+    "urlPath" : "/poster",
+    "method" : "POST",
+    "headers" : { "Accept" : { "contains" : "v.foo" }}
+  },
+  "response" : {
+    "status" : 200,
+    "body" : "Foo World"
+  }
+}
\ No newline at end of file
diff --git a/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches.json b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches.json
new file mode 100644
index 0000000000..80b7582139
--- /dev/null
+++ b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches.json
@@ -0,0 +1,11 @@
+{
+  "request" : {
+    "urlPath" : "/poster",
+    "method" : "POST",
+    "headers" : { "Accept" : { "matches" : ".*/v.bar" }}
+  },
+  "response" : {
+    "status" : 200,
+    "body" : "Bar World"
+  }
+}
\ No newline at end of file