Sasuke vs. Deidara: Sasuke analyzed the weakness of Deidara's explosives to his Lightning Release and tricked Deidara into thinking he had killed Sasuke using C4 with a genjutsu.
Naruto vs. Pain: Naruto transforming into a FRS to trick the Preta Path using the cover of smoke, and transforming into rocks to trick the Deva Path.
Jiraiya vs. Pain: Jiraiya had no knowledge of the Rinnegan's abilities, yet was able to analyze what he was able to see of them as well as come up with feints and counters to those abilities.
Definitely Shikamaru vs. Temari in the Chuunin Exam Tournament.
Shikamaru vs. Tayuya also had an incredible degree of strategy, though it's been several years since I last watched it.