First one, Ichigo couldn't fight because of Ogihci.
Second one, Grimmjaw only had one arm and wasnīt strong enough to even be in the Espada.
Third one was the first one they fought evenly and was a pretty even fight, expect when Ichigo regained his resolve because of Inoue and Ichigo manages to win stronger adversaries when he gains his resolve to fight and protect his friends (Renji, Kenpachi and now Grimmjaw).
Granted, Ichigo will do better against Ulquiorra but i still thin heīs weaker than him, thatīs why i think the rest of the team will help him namely Renji and Ishida since all these latest chapter have reinforced the friendship theme (6 hearts as one) and since everyone is there, why not?
Chad will beat the crap out of Yammi and Rukia will handle Ludbone, the Exequias leader who actually looks pretty strong.