diff --git a/org.springframework.core/src/main/java/org/springframework/util/AntPathMatcher.java b/org.springframework.core/src/main/java/org/springframework/util/AntPathMatcher.java
index 5e9b38e4698..d28f38c6a5d 100644
--- a/org.springframework.core/src/main/java/org/springframework/util/AntPathMatcher.java
+++ b/org.springframework.core/src/main/java/org/springframework/util/AntPathMatcher.java
@@ -409,7 +409,7 @@ public class AntPathMatcher implements PathMatcher {
 			if (bracketCount1 < bracketCount2) {
 				return -1;
 			}
-			else if (bracketCount1 < bracketCount2) {
+			else if (bracketCount2 < bracketCount1) {
 				return 1;
 			}
 			return 0;
diff --git a/org.springframework.core/src/test/java/org/springframework/util/AntPathMatcherTests.java b/org.springframework.core/src/test/java/org/springframework/util/AntPathMatcherTests.java
index 10a9d313e33..e2b5c036ed0 100644
--- a/org.springframework.core/src/test/java/org/springframework/util/AntPathMatcherTests.java
+++ b/org.springframework.core/src/test/java/org/springframework/util/AntPathMatcherTests.java
@@ -388,6 +388,7 @@ public class AntPathMatcherTests {
 		assertEquals(1, comparator.compare("/hotels/{hotel}", "/hotels/new"));
 		assertEquals(0, comparator.compare("/hotels/{hotel}", "/hotels/{hotel}"));
 		assertEquals(-1, comparator.compare("/hotels/{hotel}/booking", "/hotels/{hotel}/bookings/{booking}"));
+		assertEquals(1, comparator.compare("/hotels/{hotel}/bookings/{booking}", "/hotels/{hotel}/booking"));
 
 		assertEquals(-1, comparator.compare("/hotels/{hotel}", "/hotels/*"));
 		assertEquals(1, comparator.compare("/hotels/*", "/hotels/{hotel}"));