It's really impossible for Ichigo to win over Ulquiorra.
I'd say one of the captains will help him again. In this case, most likely Zaraki with Bankai can match Ulquiorra's power.

I do hope that Ichigo will lose totally just to let him know that his hollow power is not enough to stop Aizen.
He's just too arrogant and over-confident when he's in hollow mode. Always says things like "I'll finish this quick."