In my case I started with FIFA Manager 08 until 11 (IIRC), then Football Manager (SI) until 2019. Pro Cycling Manager (2016/17/18/19) , NBA2K19, WWE 2K19, Madden 19/20/21 and if you consider Blood Bowl as a sim game many years of it.
Recently I discovered DDS Pro Football and then DDS Pro Basketball.
Cheers.