I bet this happened very rarely, if ever, but I imagine it must have happened at least once or twice!
For the duel of honor that was practiced in Europe from the 16th to early 20th century, most duels saw both participants survive. As long as they both conducted themselves well, they both proved they were men of honor, so there was no real "loser", as the purpose of the duel of honor wasn't to prove a right and wrong person, but to demonstrate the honorable masculinity of the men involved. I must run, but I have several answers here that explore this in more detail.