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Hmm, here's a few:

Scoring on a goalkeeper punt in Goal on NES.

Walking to my friend's house almost daily to borrow LoZ: ALTTP for a few hours. It was so hard I had to borrow it many times to finally finish it.

Beating Secret of Mana (over and over) with my older brother on SNES. For some reason, we never bought this game. We just kept renting it every weekend and beating it all over again.