Match 1: Revan vs. Demetrius Zaarin
Zaarin did stalemate Thrawn for a while. A long while. It wasn't an easy battle for either opponent. He was also skilled enough to have the Emperor abducted. We hear of Revan's brilliance often, but I'm not aware of any specifics. And given that Thrawn > Revan by a bit, I'm inclined to say that it could go either way, but I'm leaning towards Zaarin, actually.
Match 2: Zsinj vs. Yoda
Yoda is sheer pwnage - but Zsinj was a big pain in the ass for the New Republic - and retook a quarter of the galaxy by himself. Zsinj is Yoda's tactical superior by a mile, but I think that perhaps Yoda's incredible wisdom and foresight may help.
Match 3: Count Dooku vs. Darth Vader
Eh. Count Dooku is the arrogant chess-playing type, but then again, he was only a pawn in the end (lol). Then again, so was Vader. But, Vader has shown extreme skill in tactics. He was the supreme commander of the Imperial Starfleet. He takes this.
Match 4: Traya vs. Ackbar
As with the case with Yoda vs. Zsinj, Ackbar is Traya's tactical superior by about two miles, but Traya is an extremely superb manipulator and possesses amazing foresight. Perhaps this, as with Yoda and Palpatine, would be an advantage?
Match 5: Grievous vs. Jan Dodonna
Both are skilled tactitions, but I'm leaning more with the coolest tactition (outside Thrawn) in the SW universe, Grievous, due to his skills shown during the Clone Wars.
Match 6: Sidious vs. Oppo Rancisis
Rancisis was heralded (in Cloak of Deception) for his tactical skills, and Sidious left the military tactics to his underlings. However, he is the greatest manipulator in Star Wars, and also possesses great foresight. Perhaps this would help him, as with Yoda and Traya.
Match 7: Thrawn vs. Keeramak
I echo Advent. Thrawn WTFpwns this tournament.
Match 8: Cassus Fett vs. Sev'rance Tann
Tann. Dooku let her be in charge for a reason.