I'm not sure if this is a bug or not, but it seems like one to me. You can bring your wingmen with you into the arena.
I had Volkov from Korolov, and then went to the arena. It's tricky maneuvering to get him in, but if you position yourself right while you drift, you can get him into the arena. Then you go talk to the arena station, and you can start the match with him in there with you.
If it's not a bug that you can bring wingmen, then it's a lot harder than it should be to maneuver them past the force fields, since it's pretty awkward to get them in.
