I think Itachi let him win.

it was obvious right

He lost on purpose to let Sasuke be the "hero" of the village. He also thought by doing so, that Sasuke would return to his normal life in the village. That didnt really turn out like Itatchi had planned.

@animeanimal

I Agree there's too much fact's pointing toward him not even trying like Zetsu said "what's wrong with Itachi he should of been bale to dodge the shuriken justu no problem." Also Itachi purposely stopped takeing his medicine a few days before his fight with Sasuke so he would lose on purpose because if Itachi was to use his full power Sasuke wouldn't of broken out of Itachi beloved Tsukyomi. and Itachi left himself open on purpose like he really wasn't trying

of corse itachi let sasuke win, it even said so in the manga >.>

Itachi was obvious letting Sasuke to win...
so what Sasuke's to be proud of...

There is no WAY that someone like Sasuke would win against Itachi.(no offense) It's SO obvious that Itachi was holding back!