Darth Caedus/TCW Maul vs. Anakin Skywalker/Count Dooku

Round 1: Lightsabers only

Round 2: Force fight

Round 3: All out fight

Latter team with moderate difficulty all rounds

This is actually an interesting fight. I'd give it to the first team. Caedus is almost on the level of Luke as a duelist, and given how Dooku fell against Anakin and how he seems to be terrified of Palpatine, I think it's safe to say that the gap between him and Dooku is greater than the gap between Anakin and Maul.

Of course, maybe "Zonakin" exists and he dispatches Maul in like 15 seconds, but even then I'd give Caedus a respectable shot at soloing. I contend that the Dooku-tier is really far below the Sidious-tier, which Caedus seems to be hovering around (this is necessary given a chain of powerscaling from Dooku -> Anakin -> Obi Wan -> Oppress compared to Sidious vs. Oppress, for example, and to keep Sidious > Vitiate).

I don't know. Probably team 1 but I could see team 2 taking it if Dooku's paired off against Caedus and Anakin is paired off with Maul.

I would say maul can hold out long enough against either of team 2 for caedus to beat the other with superior force powers and dueling ability
Then even if maul has died by then team 1 cleans up

Definitely team 1.

Team 1, Caedus is MVP here and is decently superior to Anakin and Dooku. Maul, meanwhile, can hold out long enough for Caedus to bring his superior abilities to bear and bring Team 1 the victory.