diff --git a/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/RequestMappingInfo.java b/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/RequestMappingInfo.java
index 445f55f5a8..a9cf31bb3e 100644
--- a/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/RequestMappingInfo.java
+++ b/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/RequestMappingInfo.java
@@ -19,6 +19,7 @@ package org.springframework.web.servlet.mvc.method;
 import java.util.List;
 import javax.servlet.http.HttpServletRequest;
 
+import org.springframework.http.HttpMethod;
 import org.springframework.util.PathMatcher;
 import org.springframework.util.StringUtils;
 import org.springframework.web.accept.ContentNegotiationManager;
@@ -238,7 +239,15 @@ public final class RequestMappingInfo implements RequestCondition<RequestMapping
 	 */
 	@Override
 	public int compareTo(RequestMappingInfo other, HttpServletRequest request) {
-		int result = this.patternsCondition.compareTo(other.getPatternsCondition(), request);
+		int result;
+		// Automatic vs explicit HTTP HEAD mapping
+		if (HttpMethod.HEAD.matches(request.getMethod())) {
+			result = this.methodsCondition.compareTo(other.getMethodsCondition(), request);
+			if (result != 0) {
+				return result;
+			}
+		}
+		result = this.patternsCondition.compareTo(other.getPatternsCondition(), request);
 		if (result != 0) {
 			return result;
 		}
@@ -258,6 +267,7 @@ public final class RequestMappingInfo implements RequestCondition<RequestMapping
 		if (result != 0) {
 			return result;
 		}
+		// Implicit (no method) vs explicit HTTP method mappings
 		result = this.methodsCondition.compareTo(other.getMethodsCondition(), request);
 		if (result != 0) {
 			return result;
diff --git a/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/RequestMappingInfoTests.java b/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/RequestMappingInfoTests.java
index 879237584a..c36f8c53b7 100644
--- a/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/RequestMappingInfoTests.java
+++ b/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/RequestMappingInfoTests.java
@@ -34,6 +34,7 @@ import static org.junit.Assert.assertNotEquals;
 import static org.junit.Assert.assertNotNull;
 import static org.junit.Assert.assertNull;
 import static org.springframework.web.bind.annotation.RequestMethod.GET;
+import static org.springframework.web.bind.annotation.RequestMethod.HEAD;
 import static org.springframework.web.servlet.mvc.method.RequestMappingInfo.paths;
 
 /**
@@ -171,6 +172,27 @@ public class RequestMappingInfoTests {
 		assertEquals(noMethods, list.get(2));
 	}
 
+	@Test // SPR-14383
+	public void compareToWithHttpHeadMapping() {
+		MockHttpServletRequest request = new MockHttpServletRequest();
+		request.setMethod("HEAD");
+		request.addHeader("Accept", "application/json");
+
+		RequestMappingInfo noMethods = paths().build();
+		RequestMappingInfo getMethod = paths().methods(GET).produces("application/json").build();
+		RequestMappingInfo headMethod = paths().methods(HEAD).build();
+
+		Comparator<RequestMappingInfo> comparator = (info, otherInfo) -> info.compareTo(otherInfo, request);
+
+		List<RequestMappingInfo> list = asList(noMethods, getMethod, headMethod);
+		Collections.shuffle(list);
+		Collections.sort(list, comparator);
+
+		assertEquals(headMethod, list.get(0));
+		assertEquals(getMethod, list.get(1));
+		assertEquals(noMethods, list.get(2));
+	}
+
 	@Test
 	public void equals() {
 		RequestMappingInfo info1 = paths("/foo").methods(GET)