diff --git a/mypy/subtypes.py b/mypy/subtypes.py
index a280c217cd8a7..9848cb45154b8 100644
--- a/mypy/subtypes.py
+++ b/mypy/subtypes.py
@@ -249,13 +249,19 @@ def visit_overloaded(self, left: Overloaded) -> bool:
                     return True
             return False
         elif isinstance(right, Overloaded):
-            # TODO: this may be too restrictive
-            if len(left.items()) != len(right.items()):
-                return False
-            for i in range(len(left.items())):
-                if not is_subtype(left.items()[i], right.items()[i], self.check_type_parameter,
+            # Ensure each overload in the left side is accounted for.
+            sub_overloads = left.items()[:]
+            while sub_overloads:
+                left_item = sub_overloads[-1]
+                for right_item in right.items():
+                    if is_subtype(left_item, right_item, self.check_type_parameter,
                                   ignore_pos_arg_names=self.ignore_pos_arg_names):
+                        sub_overloads.pop()
+                        break
+                else:
+                    # One of the overloads was not present in the right side.
                     return False
+
             return True
         elif isinstance(right, UnboundType):
             return True
diff --git a/test-data/unit/check-classes.test b/test-data/unit/check-classes.test
index 1dd3353ec903c..36c66a906001d 100644
--- a/test-data/unit/check-classes.test
+++ b/test-data/unit/check-classes.test
@@ -1419,23 +1419,6 @@ class B(A):
 [out]
 tmp/foo.pyi:8: error: Signature of "__add__" incompatible with supertype "A"
 
-[case testOverloadedOperatorMethodOverrideWithSwitchedItemOrder]
-from foo import *
-[file foo.pyi]
-from typing import overload, Any
-class A:
-    @overload
-    def __add__(self, x: 'B') -> 'B': pass
-    @overload
-    def __add__(self, x: 'A') -> 'A': pass
-class B(A):
-    @overload
-    def __add__(self, x: 'A') -> 'A': pass
-    @overload
-    def __add__(self, x: 'B') -> 'B': pass
-[out]
-tmp/foo.pyi:8: error: Signature of "__add__" incompatible with supertype "A"
-
 [case testReverseOperatorMethodArgumentType]
 from typing import Any
 class A: pass
@@ -2494,6 +2477,33 @@ reveal_type(f(BChild()))  # E: Revealed type is 'foo.B'
 [builtins fixtures/classmethod.pyi]
 [out]
 
+[case testSubtypeWithMoreOverloadsThanSupertypeSucceeds]
+from foo import *
+[file foo.pyi]
+from typing import overload
+
+
+class X: pass
+class Y: pass
+class Z: pass
+
+
+class A:
+    @overload
+    def f(self, x: X) -> X: pass
+    @overload
+    def f(self, y: Y) -> Y: pass
+
+class B(A):
+    @overload
+    def f(self, x: X) -> X: pass
+    @overload
+    def f(self, y: Y) -> Y: pass
+    @overload
+    def f(self, z: Z) -> Z: pass
+[builtins fixtures/classmethod.pyi]
+[out]
+
 [case testTypeTypeOverlapsWithObjectAndType]
 from foo import *
 [file foo.pyi]