diff --git a/base/compiler/tfuncs.jl b/base/compiler/tfuncs.jl
index b5e869ba7370a5..050d18fa1dc1bf 100644
--- a/base/compiler/tfuncs.jl
+++ b/base/compiler/tfuncs.jl
@@ -392,7 +392,7 @@ function typeof_tfunc(@nospecialize(t))
         a = widenconst(typeof_tfunc(t.a))
         b = widenconst(typeof_tfunc(t.b))
         return Union{a, b}
-    elseif isa(t, TypeVar) && !(Any <: t.ub)
+    elseif isa(t, TypeVar) && !(Any === t.ub)
         return typeof_tfunc(t.ub)
     elseif isa(t, UnionAll)
         return rewrap_unionall(widenconst(typeof_tfunc(unwrap_unionall(t))), t)
diff --git a/test/compiler/compiler.jl b/test/compiler/compiler.jl
index 791c73a61f7dbf..b6d445a3516f46 100644
--- a/test/compiler/compiler.jl
+++ b/test/compiler/compiler.jl
@@ -1339,6 +1339,12 @@ let egal_tfunc
     @test egal_tfunc(Union{Int64, Float64}, AbstractArray) === Const(false)
 end
 
+using Core.Compiler: typeof_tfunc
+@test typeof_tfunc(Union{<:T, <:Real} where T<:Complex) == Union{Type{Complex{T}} where T<:Real, Type{<:Real}}
+
+f_typeof_tfunc(x) = typeof(x)
+@test Base.return_types(f_typeof_tfunc, (Union{<:T, Int} where T<:Complex,)) == Any[Union{Type{Int}, Type{Complex{T}} where T<:Real}]
+
 function f23024(::Type{T}, ::Int) where T
     1 + 1
 end