As a player: soph year in college playing at an NAIA school, coached by a guy who was also the football coach and had not picked up a bat since he was 12 years old. We play Lewis-Clark St., then as now an NAIA powerhouse. Our record that year was something like 5 -25. We had some talent in the outfield but we were not a strong team. Played L-C at home in a dbl header on an open weekend midway through our season. Had a two run lead going into the top of the 7th in the first game. Then they scored ten runs and the party was over.
I pitched the second game of the set and they scored 4 runs in the first two innings. Between innings Coach says I really don't have anyone else that can go more than an inning. Can you hang in there? Sure, I say. Somehow manage to hold them scoreless from that point, largely because they were hitting shots right at our defense. We scratch back a run at a time and by the seventh we're tied up 4-4. I'm still throwing though I have no idea how I've lasted so long, and no real hope of surviving what I was sure was gonna be another 7th inning onslaught. First guy up hits a towering fly ball to left field that the our LF catches at the fence. Next guy up crushes a liner to the Right centerfield gap. I swear it never got more than ten feet off the ground and carried and carried. Our CF, who could run like the proverbial deer, catches up to the ball at the fence and sticks his mitt out. The fence is one of those old wire and balsa wood slat things that get rolled up when they're not needed, so it's very light weight and has a lot of vertical seams. As it happens he hits one of the seams as he catches the ball and blasts through the fence at the same time, shattering it. So now there's two outs and literally a hole in the fence. L-C State's version of Paul Bunyan comes up and smashes another ball in the same area of right/center and gets a ground rule double. Coach waddles out and says, "you've about had it, haven't you?" I said to the catcher, "give me the ball. It's my game," all the while thinking "What am I doing out here?" But Coach let me keep the ball and we get the last guy on a routine grounder to second. We ultimately win in the bottom of the seventh on a walk, a steal, a groundout to second that advances the runner and a sacrifice fly. L C State finished second in that year's NAIA world series and had a 48-11 record. I don't even want to talk about how we finished.
As a dad: Having both older sons start a few games together in the outfield for their varsity team (soph and sr. yr. respectively). Both are still playing CF, one a soph in college, and the other a senior in HS.
Watching the glee on my youngest son's face the first time he ever pitched in a live game. I think he was 9 years old. Now he's a freshman, likely to be on JV and still loves to pitch.
Hard to pick just these because the whole experience is just so much fun (most of the time!).