Here is a year-by-year list of champions and runners-up by sport:
For the record, my first recollection of a Philadelphia team in a championship game was the 1979-80 Philadelphia Flyers, so if you start my sports fan timeline at 1980. Looking back, I had a pretty good eight-year run of watching my teams in the championship (although not many of them ended with my team hoisting the trophy). As far as win/loss records in championships during that stretch, it broke down like this: Phillies 1 win, 1 loss, 76ers 1 win, 2 losses, Flyers 3 losses, and the Eagles 1 loss. In total, there were nine championship appearances in those eight seasons and only two championships to show for it; talk about heartbreak! In the years since, the Philadelphia teams have managed to bring home one additional championship in seven tries.
Using the comments below, tell me how good/bad your city or team has been over the last half century.