That may work. I think circling away from the left and making Conor chase him...not allowing Conor to be a counter puncher, which he is great at, until conor tires is a good plan. Conor will gas after 3 rounds, and assuming the fight is 5 being a main event, tho I dont know if it is a 5 rounder, making it to the 4th is cowboys best chance.
I dont think he is at a level on tds to get Conor down early. I dont think he can successfully clinch and tire Conor against the cage either during the first 3. Donald has very good kicks, but they do use a lot of energy. He should resist throwing to many until later in the fight with the exception of leg kicks. Use them to open up the high kick later in the fight. He should also look for an opportunity to get Conor to the ground after the 2nd round but not push too hard for it until the 4th. If Conor isn't tired I dont see donald taking him down unless Conor gets wobbled somehow.
Cowboy has a shit, but I'm not so sure he won't just go in trying to please the fans. He isn't an legit challenger for the belt at this point, so being calculating and using such a gameplan may not be in his mind at all. He also may believe he can knock Conor out. He should want to win, because he will get another red panty night in the rematch conor will insist upon
I guess it depends on cowboys thoughts on how long he wants to fight and if he even cares about winning, or it's all about the check. When I know he drinks budcraper even while training and doing camps, I cant think he takes it too seriously or cares about winning and moving up the ladder.