diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 7abcf8feadc5..ae2a4907e0c2 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -1129,6 +1129,7 @@ def check_overload_call(self,
         erased_targets = None  # type: Optional[List[CallableType]]
         unioned_result = None  # type: Optional[Tuple[Type, Type]]
         unioned_errors = None  # type: Optional[MessageBuilder]
+        union_success = False
         if any(isinstance(arg, UnionType) and len(arg.relevant_items()) > 1  # "real" union
                for arg in arg_types):
             erased_targets = self.overload_erased_call_targets(plausible_targets, arg_types,
@@ -1142,18 +1143,26 @@ def check_overload_call(self,
                                                  arg_messages=unioned_errors,
                                                  callable_name=callable_name,
                                                  object_type=object_type)
-                if not unioned_errors.is_errors():
-                    # Success! Stop early.
-                    return unioned_result
+                # Record if we succeeded. Next we need to see if maybe normal procedure
+                # gives a narrower type.
+                union_success = unioned_result is not None and not unioned_errors.is_errors()
 
-        # Step 3: If the union math fails, or if there was no union in the argument types,
-        #         we fall back to checking each branch one-by-one.
+        # Step 3: We try checking each branch one-by-one.
         inferred_result = self.infer_overload_return_type(plausible_targets, args, arg_types,
                                                           arg_kinds, arg_names, callable_name,
                                                           object_type, context, arg_messages)
         if inferred_result is not None:
-            # Success! Stop early.
-            return inferred_result
+            # Success! Stop early by returning the best among normal and unioned.
+            if not union_success:
+                return inferred_result
+            else:
+                assert unioned_result is not None
+                if is_subtype(inferred_result[0], unioned_result[0]):
+                    return inferred_result
+                return unioned_result
+        elif union_success:
+            assert unioned_result is not None
+            return unioned_result
 
         # Step 4: Failure. At this point, we know there is no match. We fall back to trying
         #         to find a somewhat plausible overload target using the erased types
diff --git a/test-data/unit/check-overloading.test b/test-data/unit/check-overloading.test
index 54b01412d4ba..c74ec5e32958 100644
--- a/test-data/unit/check-overloading.test
+++ b/test-data/unit/check-overloading.test
@@ -3611,6 +3611,20 @@ class Wrapper:
 
 [builtins fixtures/staticmethod.pyi]
 
+[case testUnionMathOverloadingReturnsBestType]
+from typing import Union, overload
+
+@overload
+def f(x: Union[int, str]) -> int: ...
+@overload
+def f(x: object) -> object: ...
+def f(x):
+    pass
+
+x: Union[int, str]
+reveal_type(f(x))  # E: Revealed type is 'builtins.int'
+[out]
+
 [case testOverloadAndSelfTypes]
 from typing import overload, Union, TypeVar, Type