In high school, I think I won two varsity 3200 meter races. I don't believe I ever won a 1600 or 800 meter race.
Didn't run in college, but I won a 5k the fall of my freshman year.
I could have probably won quite a few local 5k's through the years, as most seem to be won in fairly slow times (mid 17's to 19 minutes), but I choose to run races that I have no chance to win. I'd rather finish 50th in a competitive half marathon than finish 1st in an non-competitive 5k.