Tobi said it himself that if he hadn't kept secrets he would have been dead because of itachi and healthy Itachi should have more chakra but who knows add in a character that could possibly help out like naruto or sasuke and Tobi might be defeated
As tobi so bluntly put it. "itachi would have beaten me if he knew my secret" at the time when His amaterasu came out of Sasuke eyes. So if itachi knew about tobi ability at the time he mostly would have.