1. The trio wins pretty easily. Cade dispatches either one decisively, the other two dogpiles the second guy.
2. Win in a good fight.
3. Full random, probably the brothers.
Maul vs. Cade, Savage vs. Kol+Nat - Maul can take out Cade in a good contest, but Cade doesn't stand an actual chance, although he will put up a fight. The other two are massively inferior to Savage; neither Kol nor Nat hold anything on him, but that's 2v1 so they can give him a run for his money in the meantime. There are really narrow chances that these two can defeat Savage before Maul dispatches Cade, but that's possible and offers the team a legit chance.
Maul vs. Kol+Nat, Savage vs. Cade. Maul creams his opponents way before Cade can take out Savage; Cade wins, but it's a far closer combat than Maul vs. the duo. Still, with lucky timing, the Skywalker team can prevail.
Maul vs. Cade+Nat, Savage vs. Kol - Savage deals with his opponent way before Maul's fight reaches any conclusion.
4. Any duo Obi-Wan faces will never be able to accomplish anything before Anakin stomps the remaining combatant. Obi-Wan defeats everybody individually, and probably defeats any duo in a narrow contest. Anakin defeats everybody individually, and defeats any duo too. There are no matchups in which the team holds any chance. Obi-Wan and Anakin 10/10.