Apollo Creed (Rocky IV):
Win the "Apollo Creed vs. Ivan Dragon" historical fight.
Win the "Rocky Balboa vs. Clubber Lang 1" historical fight.
Win the "Clubber Lang vs. Rocky Balboa 2" historical fight.
Mason "The Line" Dixon:
Win the "Rocky Balboa vs. Mason Dixon" historical fight.
Win the "Mason Dixon vs. Rocky Balboa" historical fight.
Thanks to Revolution Readers mori and daveos!