Never get tired of this question every time Oda takes a week break in the last 2-3 years.
–- Update From New Post Merge ---
Then I guess you mean Kyros defeated Dofla once, right? He had 3000 wins, never lost a fight, and only got wounded once. It means he defeated the person who managed to wound him.
But on the other hand, it would be fun to see how Dofla fights someone who already kicked his ass once.Don't see why the person who wounded Kyros has to be relevant for this arc and not relevant for future arcs or main plot line in general.
Yeah I agree, that and didn't Doflamingo's first act after returning to the country is to talk to King Riku and then the people of Dressrosa? If he fought in the Colosseum, wouldn't people know? or if King Riku watches all his fights, he'd also recognize him.
It's obvious that Kyros got wounded during his 3000th battle or before that since that statue provides people the fact that he was wounded only once.
If we look at the timeline, Kyros was 15 years old + 4 years for the 1000 wins, he'd be 19 years old at the end of this chapter. IF we take the fact that the wins follows the same rate/time, 4 more years for his 2000th win (23 years old) and 4 more years after that for his 3000th (27 years old). He "retired" 20 years ago so his age would be around 47 years old.
Here's the bit more interesting info: If the timeline above is correct, after his 2000th win it'd be 24 years ago, the same time when Roger was executed and the Great Pirate Age started. Whether it be Roger himself whom wounded him before his 2000th win, or him being wounded by any one of the many other pirates resulting after Roger's execution. It's quite clear that there are many possibilities, Mihawk and Shanks for instance (we saw them at the execution) - Mihawk WOULD be 4 years younger than Kyros (he'd be 19-23 by Kyros' 2000th-3000th win), while Shanks is 4 years younger than Mihawk and would be 8 years younger than Kyros (he'd be 15-19 by Kyros' 2000th-3000th win). That would mean it is NOT impossible that a 19-23 year old Mihawk manage to wound Kyros whom is 4 years older than him and with 2000-2999 wins already under his belt - that goes for Shanks as well.