This game might have been mentioned before, I forget its name. It used baseball cards, and the results depended on the player's stats on the back of his card (HR in last season and career AVG.). You roll two dice, look for the column that the hitter fits under (front side had 0-20 HR, back side had 21 or more HR), and then the result of the roll tells you what you get. For example, 7 was always a strikeout. Does anyone know what it was called?
Every Sunday my grandma would bring me a pack of baseball cards to make teams out of for it, and then for Christmas one year she got me a complete set (Fleer 1990 I think, they were bright yellow cards). Whenever I wasn't at practice, I was sitting on the floor in my room playing that game. I got the MLB schedule out of the newspaper and attempted to play out the entire season. I would keep score of a game, managing both teams, then go input the stats into a spreadsheet on the computer. I would also make league leaderboards, league records, etc. I only got through about the middle of April, after doing that for what seemed like the whole summer.
As far as other games, I played what I think was the first NES baseball game, Major League Baseball. That was always fun, except the little glitch that allowed you to go into the crowd to catch a foul ball.
OOTP4 was my first PC game. Before that I had various console games, none of which held my attention for very long.