Ulquiorra: Crows? Who are you?
Itachi: Uchiha Itachi.

Yeah that was lame. Anyway, this is the first part of my Akatsuki vs. Espada project, Itachi vs. Ulquiorra. Let's see who would win.

Itachi:

-Sharingan.
-Weapons.
-Fire style ninjutsu.
-Susano'o.
-Genjutsu.
-Taijutsu.
-Amaterasu.
-Shawdow Clones.
-Substitution Jutsu.

Ulquiorra:

-Cero.
-Speed.
-Sword.
-Power.
-Defense.
-Tough Skin.
-Release form.
-Taijutsu.

When you really come down to it, we really don't know who would win. We haven't seen Ulquiorra's zanpakutō. But even if we do see it, Itachi could probably block and attack it with Susano'o. If Ulquiorra even did get caught in Itachi's genjutsu then it's pretty much over. And if Ulquiorra used Cero, Itachi could just dodge it. If Ulquiorra had tried to attack Itachi with his sword and his speed then Itachi would probably get hit or he would have used a subtitution jutsu. Itachi would probably use Fire style jutsu's but then Ulquiorra would have just deflected it. BUt if Itachi used Amaterasu the I don't think Ulquiorra would have had a snow balls chance in hell. So at the end I think we have a winner, even though we don't really know.

The probable winner:
Uchiha Itachi