One contest always. Anything more than that looks so appallingly complex I didn't even read your message properly :)
Also, "Side A wants to keep a distance and win by peppering the opposition with arrows" - I personally would look to step back some to devise a goal, looks too mechanical to me. "The Archers want to humiliate the pompous knights and gain glory" is ever so much more flexible and, IMO, more likely to be entertaining.
If you split things up, you also run the risk of having a great, fantastic, fantabulous extended contest (or its opposite) and then having to say to the players, "Right, that's step one. Now on to step two."
As I almost always seem to, I strongly recommend a dose of CAPES (the game). - Player A narrates a building falling on top of Player B's character. Whatever Player A has narrated makes not a jot of difference to what abilities Player B is allowed to narrate next. Player B wants to use his/her best ability now, which is Loves Fido the Dog? Player B narrates how Fido the Dog leads his/her character to safety just as thebuilding is collapsing and Player A is back to square 1 (or rather, is wherever the dice have led the game).
So, the horsemen have closed but the archers still want to use the Archery skill? I'd say let them but make them narrate how they do so in this situation and damn the situational modifiers. The AP tell you about the situation (If the horsemen close, that's represented in the AP, why limit the abilities too - that's a double dose?). I think it makes for interesting narration as you have to be a bit resourceful in using the archery skill in that closed situation. Maybe an improvisational modification (the archers use the bows to trip the horses say).
Just my thruppence 'orth.
Sam.
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