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 bbb5f36d9a..d3e93e3814 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
@@ -35,6 +35,8 @@ import java.io.IOException;
 import java.nio.charset.Charset;
 import java.util.ArrayList;
 import java.util.Arrays;
+import java.util.Collections;
+import java.util.Comparator;
 import java.util.List;
 
 import com.github.tomakehurst.wiremock.common.Json;
@@ -43,7 +45,6 @@ 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;
@@ -151,7 +152,7 @@ public class WireMockRestServiceServer {
 	 */
 	public MockRestServiceServer build() {
 		MockRestServiceServer server = this.builder.build();
-		SortedConcurrentMappingSet mappings = new SortedConcurrentMappingSet();
+		List<StubMapping> mappings = new ArrayList<>();
 		for (String location : this.locations) {
 			try {
 				for (Resource resource : this.resolver.getResources(pattern(location))) {
@@ -164,6 +165,7 @@ public class WireMockRestServiceServer {
 						e);
 			}
 		}
+		Collections.sort(mappings, new StubMappingComparator());
 		for (StubMapping mapping : mappings) {
 			ResponseActions expect = server
 					.expect(requestTo(request(mapping.getRequest())));
@@ -247,4 +249,42 @@ public class WireMockRestServiceServer {
 		return value == null ? MediaType.TEXT_PLAIN : MediaType.valueOf(value);
 	}
 
+	private static class StubMappingComparator implements Comparator<StubMapping> {
+
+		@Override
+		public int compare(StubMapping one, StubMapping two) {
+			if (one==two) {
+				return 0;
+			}
+			int value = request(one.getRequest()).compareTo(request(two.getRequest()));
+			if (value == 0) {
+
+				// Every mapping has a url pattern, and zero or more header patterns
+				int twos = 0;
+				if (two.getRequest().getHeaders() != null) {
+					twos = two.getRequest().getHeaders().size();
+				}
+				int ones = 0;
+				if (one.getRequest().getHeaders() != null) {
+					ones = one.getRequest().getHeaders().size();
+				}
+				value = twos - ones;
+				if (value == 0) {
+					// Same number of header matchers
+					if (two.getPriority() != null) {
+						return one.getPriority() != null
+								? one.getPriority() - two.getPriority() : 1;
+					}
+					value = (int) (one.getInsertionIndex() - two.getInsertionIndex());
+				}
+			}
+			return value;
+		}
+
+		private String request(RequestPattern request) {
+			return (request.getUrlPath() == null ? (request.getUrl() == null ? "/" : request.getUrl()) : request.getUrlPath());
+		}
+
+	}
+
 }
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 59f0d0e686..070badb92a 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
@@ -68,33 +68,56 @@ public class WiremockMockServerApplicationTests {
 	public void postWithHeader() throws Exception {
 		WireMockRestServiceServer.with(this.restTemplate) //
 				.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");
+				.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");
+				.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();
+				.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 postWithMoreExactHeaderMatch() throws Exception {
+		WireMockRestServiceServer.with(this.restTemplate) //
+				.baseUrl("http://example.org") // order matters...
+				.stubs("classpath:/mappings/header-matches.json",
+						"classpath:/mappings/header-matches-precise.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");
+						.accept(MediaType.valueOf("application/v.bar"))
+						.header("X-Precise", "true").build(), String.class)
+				.getBody()).isEqualTo("Precise World");
 	}
 
 	@Test
diff --git a/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches-precise.json b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches-precise.json
new file mode 100644
index 0000000000..3ffd54ed24
--- /dev/null
+++ b/spring-cloud-contract-wiremock/src/test/resources/mappings/header-matches-precise.json
@@ -0,0 +1,11 @@
+{
+  "request" : {
+    "urlPath" : "/poster",
+    "method" : "POST",
+    "headers" : { "Accept" : { "matches" : ".*/v.bar" }, "X-Precise" : { "equalTo" : "true" }}
+  },
+  "response" : {
+    "status" : 200,
+    "body" : "Precise World"
+  }
+}
\ No newline at end of file