All the time.
I caught a big ol' brown in MT four times in one month once. Have pics from at least two of the four catches.
My ex, my brother-in-law, and I caught the same trout on the San Juan four times in one day once.
A couple years ago on opening weekend, I caught a half-pounder steelhead twice and broke him off twice in two days, all on the same fly. The two time I caught him I got back the two flies I lost in him.
A buddy of mine caught a brown trout this winter two days after I caught him and removed a tag from him.
And, I have retrieved both my flies and flies of buddies from trout and steelhead many many times.
Dennis