In the third episode of the campaign, "Take Part in the Underground Fight", use the following combinations:
T-Shirt + Wounded Hand = Industrial District
Explore + Industrial District = Abandoned Warehouse, Fight Club
Explore + Abandoned Warehouse = Abandoned Warehouse, Knocked Tooth
Explore + Fight Club = Coach Mickey
Coach Mickey + Money = 23:00, Block, Left Hook, Right Hook, Uppercut
23:00 + Abandoned Warehouse = Underground Fight
Explore + Underground Fight = Bar, Fight, Mike, Ronald
Fight + Mike = Mike's Attack
Block + Mike's Attack = Mike's Defense
Mike's Defense + Uppercut = Apollo, Fight, Knockout, Money
Bar + Money = Beer
Beer + Ronald = Kind Ronald
Apollo + Fight = Apollo's Attack
Apollo's Attack + Block = Apollo's Defense, Broken Rib
Apollo's Defense + Right Hook = Beaten Apollo
Beaten Apollo + Right Hook = Fall, Finish of Apollo, Second Round
Fall + Second Round = Golden Watch, Money
The achievement should then unlock