Board Thread:Naruto Discussions/@comment-25516007-20141008201906/@comment-1018594-20141009020655

Ebisu said Jiraiya was the only one who could kill Orochimaru when he invaded Konoha. Pain said the only reason he was able to defeat Jiraiya is because he surprised him with the multiple Paths. Itachi also said the best he and Kisame could do against Jiraiya would end in a draw, assuming Itachi knew how to use Susanoo and Kisame could fuse with Samehada in Part 1. He also assumed that calling in the rest of Akatsuki wouldn't help their chances. Obito even refused to have Kabuto reincarnate him, saying that it was too risky; there's a good chance he would have been able to break Kabuto's control.

Kakashi, who Pain also described as a major threat to him, admitted that he stood no chance against Orochimaru in Part 1. The Fourth Kazekage had to subdue Shukaku like every other week with his Gold Dust, and Orochimaru killed him effortlessly. Sasuke admitted that he was only able to seal Orochimaru because he was weakened at the time, and once he regained the use of his arms, Orochimaru was able to hold off the Ten-Tails nonchalantly. He also gained Wood Release from the White Zetsu he's using as his new body, and it's safe to assume that this new body would allow him to use Senjutsu as well.

If we factor in the databooks, Jiraiya is a 35.5 and Orochimaru is a 35 out of a possible 40. However, neither of them were at their full potential when those databooks were released. At the very best, I'd say it's a tie. It's more likely that they'd both kill each other than one having a clear advantage.