My sporting life is divided into three phases: The Pittsburgh, San Francisco and Chicago eras.
Pittsburgh (mid 70s-mid 80s); 2 Super Bowls and the intervening World Series. I think 11 is absolutely the optimal age to have this happen! :DI have no conscious memories of the first two Steelers SBs, so don’t count them.
San Francisco (mid 80s-early oughts): 3 Super Bowls (didn’t follow them for the first 2), one traumatic World Series collapse.
Chicago: (early 00s- present) diddly so far (I root for the Cubs and don’t care about the Blackhawks, arrived too late for the Jordan era), unless you want to count one Supporters Shield and two US Open Cups for the Fire, which you probably don’t.
My alma mater, the University of Oregon, has won five Pac-10/12 championships and one Rose Bowl, but never the big crystal football. In men’s basketball, we have one Pac-whatever regular season title and three conference tournament championships. Still waiting for some company for that lonely 1939 NCAA Championship banner in the rafters. Those are the only two college sports I follow. I also root for Northwestern, which doesn’t help.
Recently I have also decided to adopt Tottenham Hotspur, and have little fear of being accused of being a bandwagon jumper.
So, grand total 5 Super Bowls, 1 World Series. I would count the Rose Bowl as a comparable achievement, plus the 2001 Fiesta Bowl (Ducks won the conference, but didn’t go to the Rose Bowl as it was hosting the BCS title game that year) for a total of 8.