An odd one this but that’s football… On this day (21 November) 1960 Portsmouth became the first side ever to beat Manchester City in the League Cup. The round three tie ended 2-0 before a Fratton Park crowd of 10,386. Future City boss Ron Saunders scored both Portsmouth goals. Ah well! Here’s a contemporary report of the game (it seems Trautmann got into a bit of a dispute with the crowd and the police had to intervene!)
You can read about Ron Saunders’ time at City here:
Gary James' Football Archive 