There are two clubs in England who have both won the F.A Cup, which by the way is the oldest Club played for in England it goes back roughly to the year 1871, or so. These two famous F.A. Cups were called The Goliath and David matches. As they were two clubs with small budgets and no famous footballer in their clubs. 1) Portsmouth defeated the mighty Chelsea team which had Didier Drogba and Franck Lampard. The winner of the winning goal was the Nigerian striker Kanu. And as Portsmouth were in big financial problems, their yearly loss was far to much and they were under the hand of the administrator, and so according to the rules , any club which falls into the hands of the administrator 2, the club faces nine points deduction and is automatically demoted to the next league. 22) Wigan Athletic in the year 2013, defeated the oil rich Arab club Manchester City by the score of 1-0, it was Watson goal. But by the last day of the season they were relegated as well.