Fun topic!
I started with board games, though as a '90s kid, this was moreso a matter that it was what my Dad shared and played with me. Specifically, that meant All-Star Baseball (I saw someone else here had played that, too!), and Bowl Bound College Football (the old board game). Played a lot of sports video games as a kid and teen, and then got more into the sports sim world in college by searching online for Bowl Bowl College Football (the old board game) and stumbling across Bowl Bound College Football (the more modern Grey Dog sim game). Played in some leagues, and also played and ran a soccer league using the freeware ESMS+ software.
Not a lot of time to play anymore, but I like trying to develop stuff, and I'm hoping that as my young son gets older, I can do a 3rd generation of All-Star Baseball with him.