Sportsmaster wins the first round. His strength,striking,and durability far exceed Oliver's its not even funny. But in the second round he's likely to get taken out by explosive arrows. Tho he does scale above someone who's an arrow timer.
@worldsgreatest: Didn't Oliver mulitple times outsmarted Derek Samphson who is already stated to be super meta by Felicity as Derek got contact with unusuall toxins ?
Outsmart isn't the word I'd use. Derek Sampson just couldn't fight as well as Ollie could. Sportsmaster has 20+ years of fighting experience and was stated to be the best fighter Pat has ever seen who himself have encountered dozens of superheros.
Not to mention his durability is off the charts and so is his strength. He scales to his wife who could take concrete vaporizing blasts with little to no damage aside from simply being K.O/d. Clash evenly with a punch that can go through trees and make large dents and move pick up trucks. Throw a person 20 feet with one arm while in midair,send someone flying a good seven feet with a punch,send someone flying 20 feet with his baseball bat etc.