diff -r 06161ebf74ee -r 99e275768a6c Lib/test/test_dict_jy.py
--- a/Lib/test/test_dict_jy.py	Mon May 19 09:02:22 2014 +0100
+++ b/Lib/test/test_dict_jy.py	Thu May 22 22:07:01 2014 -0700
@@ -120,6 +120,13 @@
         x.put((1,2), "xyz")
         y = dict(x)
         self.assertEqual(set(y.items()), set([('a', 1), ('b', 2), ('c', 3), ((1,2), "xyz")]))
+
+    def test_hashmap_builtin_pymethods(self):
+        x = java.util.HashMap()
+        x['a'] = 1
+        x[(1, 2)] = 'xyz'
+        self.assertEqual({tup for tup in x.iteritems()}, {('a', 1), ((1, 2), 'xyz')})
+
     def test_hashtable(self):
         x = java.util.Hashtable()
         x.put('a', 1)
diff -r 06161ebf74ee -r 99e275768a6c src/org/python/core/PyJavaType.java
--- a/src/org/python/core/PyJavaType.java	Mon May 19 09:02:22 2014 +0100
+++ b/src/org/python/core/PyJavaType.java	Thu May 22 22:07:01 2014 -0700
@@ -531,11 +531,10 @@
         } else {
             dict.__setitem__("__init__", reflctr);
         }
-        for (Map.Entry<Class<?>, PyBuiltinMethod[]> entry : getCollectionProxies().entrySet()) {
-            if (entry.getKey() == forClass) {
-                for (PyBuiltinMethod meth : entry.getValue()) {
-                    addMethod(meth);
-                }
+        PyBuiltinMethod[] collectionProxyMethods = getCollectionProxies().get(forClass);
+        if (collectionProxyMethods != null) {
+            for (PyBuiltinMethod meth : collectionProxyMethods) {
+                addMethod(meth);
             }
         }
         if (ClassDictInit.class.isAssignableFrom(forClass) && forClass != ClassDictInit.class) {
@@ -920,6 +919,13 @@
         protected abstract boolean getResult(int comparison);
     }
 
+    /**
+     * Build a map of common Java collection base types (Map, Iterable, etc) that need to be
+     * injected with Python's equivalent types' builtin methods (__len__, __iter__, iteritems, etc).
+     *
+     * @return A map whose key is the base Java collection types and whose entry is a list of
+     *         injected methods.
+     */
     private static Map<Class<?>, PyBuiltinMethod[]> getCollectionProxies() {
         if (collectionProxies == null) {
             collectionProxies = Generic.map();
@@ -1005,13 +1011,32 @@
                     return Py.java2py(asMap().remove(Py.tojava(key, Object.class)));
                 }
             };
+            PyBuiltinMethodNarrow mapIterItemsProxy = new MapMethod("iteritems", 0) {
+                @Override
+                public PyObject __call__() {
+                    final Iterator<Map.Entry<Object, Object>> entrySetIterator = asMap().entrySet().iterator();
+                    return new PyIterator() {
+                        @Override
+                        public PyObject __iternext__() {
+                            if (entrySetIterator.hasNext()) {
+                                Map.Entry<Object, Object> nextEntry = entrySetIterator.next();
+                                // yield a Python tuple object (key, value)
+                                return new PyTuple(Py.java2py(nextEntry.getKey()),
+                                                   Py.java2py(nextEntry.getValue()));
+                            }
+                            return null;
+                        }
+                    };
+                }
+            };
             collectionProxies.put(Map.class, new PyBuiltinMethod[] {mapLenProxy,
                     // map IterProxy can conflict with Iterable.class; fix after the fact in handleMroError
                                                                     mapIterProxy,
                                                                     mapContainsProxy,
                                                                     mapGetProxy,
                                                                     mapPutProxy,
-                                                                    mapRemoveProxy});
+                                                                    mapRemoveProxy,
+                                                                    mapIterItemsProxy});
 
             PyBuiltinMethodNarrow listGetProxy = new ListMethod("__getitem__", 1) {
                 @Override