BR0B0T You can get extremely lucky with Cups and make it to the final whilst not being particularly good (Wimbledon, Milwall etc)
While I agree with your point overall, I can never get why people maintain Wimbledon's win in '88 is one of the biggest cup upsets ever. They finished 7th in the first division that year, and had an established reputation as being a team that made life difficult for the top sides.