I have put many hours into sports games over the years. Many times playing NHL 2001 and 2002, then NHL 04. Then NHL 06... which led to me being the official NHLDepot roster modder for NHL 06 for some time. Unfortunately, that task killed my liking of hockey video games.
Baseball games are by far my favorite. I have spent a lot of time with WSB, WSBII, Frank Thomas and the All-Star edition on Saturn. Then ESPN Baseball (2K4) on PS2 to the point where I had to rebuy the game because I wore the original disc out. I have won the World Series (or the "championship") in WSB for Game Gear as the Padres,
Triple Play Gold on the Sega Genesis as the Indians. Most other times I try to play baseball games, I would opt for full seasons... and something usually messes up.
For ESPN Baseball on the PS2, I've never been able to complete a full season. There are some bugs in the game (besides the music loop/silence bug) but one with the individual stat tables have wacky numbers in them. Like showing 400 doubles instead of 20. One thing I really loved about ESPN Baseball is that you don't have to pitch if you don't want to. You can switch sides each half inning to bat for both teams, or you can simulate half innings if you only want to bat. Roster management is decent as well.
One reason for me to slow down on ESPN Baseball was finding out about the active modding community for MVP Baseball 2005. This was after I knew that the game existed (I had played MVP Baseball 2004 on PS2) but we're talking about the PC version which was impossible to find. A friend of mine was able to find it online somewhere but it was a bit glitchy. BUT it let us install a mod to change one of the stadiums to the one in our hometown. And the practice mode always had the ball bouncing off some invisible object in the outfield. After getting MVP Baseball 2005 for PS2, I found out that was a tractor. I had also spend a short amount of time on the Loaded series (it is like NFL Blitz or NHL Hitz) but not really impressed. MLB The Show has some great presentation, but annoying GM options and I could never get it to use a custom roster on PS3. I had spent some time with Baseball Mogul and some other simulators, but what I was really looking for was something I had the whole time.
And that is Major League Manager, a game for DOS. I've been playing it monthly now since around 1993 or so when I got it for my IBM XT from Office Max. Now I'm running it in DOSBox, using modified leagues and teams, and have a PoC to fixing the player limit bug that exists in all versions of the game. To be clear, the bug will still exist, I just now have a way to refactor the rosters to allow for continued use of the software without the data becoming corrupted. I'm running through a beta build of my 2020 version, but seeing how this season hasn't happened yet, I probably won't be releasing it publicly for quite awhile.