diff --git a/jedi/evaluate/context/function.py b/jedi/evaluate/context/function.py
index 370428f3..ed295c52 100644
--- a/jedi/evaluate/context/function.py
+++ b/jedi/evaluate/context/function.py
@@ -16,6 +16,7 @@ from jedi.evaluate.base_context import ContextualizedNode, NO_CONTEXTS, \
     ContextSet, TreeContext
 from jedi.evaluate.lazy_context import LazyKnownContexts, LazyKnownContext, \
     LazyTreeContext
+from jedi.evaluate.context.typing import TypeVar
 from jedi.evaluate.context import iterable
 from jedi.evaluate.context import asynchronous
 from jedi import parser_utils
@@ -335,11 +336,21 @@ def signature_matches(function_context, arguments):
                 function_context.parent_context,
                 param_node.annotation
             )
-            return has_same_class(argument.infer().py__class__(), annotation_result)
+            return has_same_class(
+                argument.infer().py__class__(),
+                _type_vars_to_classes(annotation_result),
+            )
 
     return True
 
 
+def _type_vars_to_classes(context_set):
+    return ContextSet.from_sets(
+        context.get_classes() if isinstance(context, TypeVar) else set([context])
+        for context in context_set
+    )
+
+
 def has_same_class(context_set1, context_set2):
     for c1 in context_set1:
         for c2 in context_set2:
diff --git a/jedi/evaluate/context/typing.py b/jedi/evaluate/context/typing.py
index af8317a6..7471e9f7 100644
--- a/jedi/evaluate/context/typing.py
+++ b/jedi/evaluate/context/typing.py
@@ -391,12 +391,19 @@ class TypeVar(_BaseTypingContext):
     def get_filters(self, *args, **kwargs):
         return iter([])
 
-    def execute_annotation(self):
+    def get_classes(self):
         if self._bound_lazy_context is not None:
-            return self._bound_lazy_context.infer().execute_annotation()
+            return self._bound_lazy_context.infer()
+        if self._constraints_lazy_contexts:
+            return ContextSet.from_sets(
+                l.infer() for l in self._constraints_lazy_contexts
+            )
         debug.warning('Tried to infer a TypeVar without a given type')
         return NO_CONTEXTS
 
+    def execute_annotation(self):
+        return self.get_classes().execute_annotation()
+
     def __repr__(self):
         return '<%s: %s>' % (self.__class__.__name__, self.var_name)