diff --git a/jetty-http/src/main/java/org/eclipse/jetty/http/pathmap/PathMappings.java b/jetty-http/src/main/java/org/eclipse/jetty/http/pathmap/PathMappings.java
index 2012d5fec9c..c2871a58cab 100644
--- a/jetty-http/src/main/java/org/eclipse/jetty/http/pathmap/PathMappings.java
+++ b/jetty-http/src/main/java/org/eclipse/jetty/http/pathmap/PathMappings.java
@@ -176,16 +176,15 @@ public class PathMappings<E> implements Iterable<MappedResource<E>>, Dumpable
                             int i = path.length();
                             while (i >= 0)
                             {
-                                MappedResource<E> candidate = _exactMap.getBest(path, 0, i);
+                                MappedResource<E> candidate = _exactMap.getBest(path, 0, i--);
                                 if (candidate == null)
-                                    break;
+                                    continue;
 
                                 matchedPath = candidate.getPathSpec().matched(path);
                                 if (matchedPath != null)
                                 {
                                     return new MatchedResource<>(candidate.getResource(), candidate.getPathSpec(), matchedPath);
                                 }
-                                i--;
                             }
                             // If we reached here, there's NO optimized EXACT Match possible, skip simple match below
                             skipRestOfGroup = true;
@@ -200,14 +199,13 @@ public class PathMappings<E> implements Iterable<MappedResource<E>>, Dumpable
                             int i = path.length();
                             while (i >= 0)
                             {
-                                MappedResource<E> candidate = _prefixMap.getBest(path, 0, i);
+                                MappedResource<E> candidate = _prefixMap.getBest(path, 0, i--);
                                 if (candidate == null)
-                                    break;
+                                    continue;
 
                                 matchedPath = candidate.getPathSpec().matched(path);
                                 if (matchedPath != null)
                                     return new MatchedResource<>(candidate.getResource(), candidate.getPathSpec(), matchedPath);
-                                i--;
                             }
                             // If we reached here, there's NO optimized PREFIX Match possible, skip simple match below
                             skipRestOfGroup = true;
@@ -220,11 +218,16 @@ public class PathMappings<E> implements Iterable<MappedResource<E>>, Dumpable
                         if (_optimizedSuffix)
                         {
                             int i = 0;
+                            // Loop through each suffix mark
+                            // Input is "/a.b.c.foo"
+                            //  Loop 1: "b.c.foo"
+                            //  Loop 2: "c.foo"
+                            //  Loop 3: "foo"
                             while ((i = path.indexOf('.', i + 1)) > 0)
                             {
                                 MappedResource<E> candidate = _suffixMap.get(path, i + 1, path.length() - i - 1);
                                 if (candidate == null)
-                                    break;
+                                    continue;
 
                                 matchedPath = candidate.getPathSpec().matched(path);
                                 if (matchedPath != null)
diff --git a/jetty-http/src/test/java/org/eclipse/jetty/http/pathmap/PathMappingsTest.java b/jetty-http/src/test/java/org/eclipse/jetty/http/pathmap/PathMappingsTest.java
index 3af0a9e2563..24b417bad00 100644
--- a/jetty-http/src/test/java/org/eclipse/jetty/http/pathmap/PathMappingsTest.java
+++ b/jetty-http/src/test/java/org/eclipse/jetty/http/pathmap/PathMappingsTest.java
@@ -319,6 +319,32 @@ public class PathMappingsTest
         assertThat(p.get(new RegexPathSpec("/a/b/c")), nullValue());
     }
 
+    @Test
+    public void testServletMultipleSuffixMappings()
+    {
+        PathMappings<String> p = new PathMappings<>();
+        p.put(new ServletPathSpec("*.foo"), "resourceFoo");
+        p.put(new ServletPathSpec("*.bar"), "resourceBar");
+        p.put(new ServletPathSpec("*.zed"), "resourceZed");
+
+        MatchedResource<String> matched;
+
+        matched = p.getMatched("/a.b.c.foo");
+        assertThat(matched.getResource(), is("resourceFoo"));
+
+        matched = p.getMatched("/a.b.c.bar");
+        assertThat(matched.getResource(), is("resourceBar"));
+
+        matched = p.getMatched("/a.b.c.pop");
+        assertNull(matched);
+
+        matched = p.getMatched("/a.foo.c.pop");
+        assertNull(matched);
+
+        matched = p.getMatched("/a%2Efoo");
+        assertNull(matched);
+    }
+
     @Test
     public void testRemoveUriTemplatePathSpec()
     {