I think it's because Saber's voice actor is Winter's voice actor in the Japanese dub?
Then it doesn't belong in the Hilarious in Hindsight pool since it was already known when i uploaded this picture that Winter's Japanese voice actress was Ayako Kawasumi and the artist drew this in response to that. So unless there's another reason why this picture is in the pool, the picture will be removed from the Hilarious in Hindsight pool.