diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
index 3a234bb8a6..69efe5958a 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
@@ -256,6 +256,65 @@ static_assert(is_equivalent_to(int | Callable[[int | str], None], Callable[[str
 
 ### Overloads
 
-TODO
+#### One overload
+
+`overloaded.pyi`:
+
+```pyi
+from typing import overload
+
+class Grandparent: ...
+class Parent(Grandparent): ...
+class Child(Parent): ...
+
+@overload
+def overloaded(a: Child) -> None: ...
+@overload
+def overloaded(a: Parent) -> None: ...
+@overload
+def overloaded(a: Grandparent) -> None: ...
+```
+
+```py
+from knot_extensions import CallableTypeOf, is_equivalent_to, static_assert
+from overloaded import Grandparent, Parent, Child, overloaded
+
+def grandparent(a: Grandparent) -> None: ...
+
+static_assert(is_equivalent_to(CallableTypeOf[grandparent], CallableTypeOf[overloaded]))
+static_assert(is_equivalent_to(CallableTypeOf[overloaded], CallableTypeOf[grandparent]))
+```
+
+#### Both overloads
+
+`overloaded.pyi`:
+
+```pyi
+from typing import overload
+
+class Grandparent: ...
+class Parent(Grandparent): ...
+class Child(Parent): ...
+
+@overload
+def pg(a: Parent) -> None: ...
+@overload
+def pg(a: Grandparent) -> None: ...
+
+@overload
+def cpg(a: Child) -> None: ...
+@overload
+def cpg(a: Parent) -> None: ...
+@overload
+def cpg(a: Grandparent) -> None: ...
+```
+
+```py
+from knot_extensions import CallableTypeOf, is_equivalent_to, static_assert
+from overloaded import pg, cpg
+
+static_assert(is_equivalent_to(CallableTypeOf[pg], CallableTypeOf[cpg]))
+static_assert(is_equivalent_to(CallableTypeOf[cpg], CallableTypeOf[pg]))
+```
 
 [the equivalence relation]: https://typing.python.org/en/latest/spec/glossary.html#term-equivalent
diff --git a/crates/red_knot_python_semantic/src/types.rs b/crates/red_knot_python_semantic/src/types.rs
index dc7a789939..1047e929f0 100644
--- a/crates/red_knot_python_semantic/src/types.rs
+++ b/crates/red_knot_python_semantic/src/types.rs
@@ -6984,11 +6984,22 @@ impl<'db> CallableType<'db> {
     fn is_equivalent_to(self, db: &'db dyn Db, other: Self) -> bool {
         match (&**self.signatures(db), &**other.signatures(db)) {
             ([self_signature], [other_signature]) => {
+                // Common case: both callable types contain a single signature, use the custom
+                // equivalence check instead of delegating it to the subtype check.
                 self_signature.is_equivalent_to(db, other_signature)
             }
-            _ => {
-                // TODO: overloads
-                false
+            (self_signatures, other_signatures) => {
+                if !self_signatures
+                    .iter()
+                    .chain(other_signatures.iter())
+                    .all(|signature| signature.is_fully_static(db))
+                {
+                    return false;
+                }
+                if self == other {
+                    return true;
+                }
+                self.is_subtype_of(db, other) && other.is_subtype_of(db, self)
             }
         }
     }