I’m not sure how to answer this question.
I’m strictly baseball and grew up rooting for the Montreal Expos. When they left for Washington, after a couple of years I cheered on the Blue Jays by default, especially when they became good in 2015.
When the Blue Jays won in 1992 and 1993, I was happy but not in the way I imagined if the Expos had won. Today, I would be ecstatic if the Jays won. When the Nationals won in 2019, I didn’t even realize they were the old Expos until they won, and on what would have been their 50th anniversary. I actually was rooting for the Astros to win.
So, none of my teams won while I was actively rooting for them. At least not major league baseball. We had a Triple-A team here, the Lynx, who won the International League championship in 1995.