Is here any point in fighting an enemy more than 50 times? Like do you get more exp or items later on?
no, in fact exp rewards begin dropping off around... well they changed it recently, it used to be after 10 wins but it's higher now. and thus far there have been no additional battle loot items for wins beyond... i want to say 15? maybe 20? again, used to be 10, but that was tweaked a little bit ago.
Please disregard what Frenchi just told you on loot, that is not accurate. There is a loot tracking thread that has been around since the new changes were implemented and a google spreadsheet that covers most if not all of the challengers and loot dropped at wins up to 200, just click the different tabs at the bottom of the spreadsheet for 'normal/secret' etc. Also check the 'key' tab that will explain exp and such.