Between 60 and 80 races. Smallest was with about 18 finishers (20k on the track in 1:03 something and the last placer was timed 29 seconds slower than me). Largest? Several thousands runners, one of the rock'n'roll series in the US. It is much easier for me to win races in my 30s, than when I was in my prime, due to severe reduction in the quality of the fields. Honestly, when I was able to crack 29 in 10k, I had seldom won, although I had placed very often in top 5. Nowadays, 30flat gets me a win in most races I enter (it also helps I am not a roadie anymore and don't train and race much of the year in the US).
Breaking a tape? Yes, quite a few times, but I never thought of keeping the tape. I had even tripped over a finish tape, since it did not tear and I got entangled in it.
Now that I think of it, I had won every race I could have, without using illegal substances (I am not implying that those I could have not beaten had used them, but I know my physical limits), except for one local, albeit very large, race. When I had the ability to win that one, I was living in the US and thought it was not worth to travel back home for just that race. Now I do not possess enough finishing speed to outkick the Kenyan roadies that enter this race every year. I would trade all my wins for just one in this race. It is akin to Boston marathon in my country. If you are not listed among the winners on the statute, you are not considered as a good runner among the peers.
The wins that seem inconsequential at the time, may turn out to be the most cherished over the time.