Well, this is healthy Itachi so he should be fine, but with the opponents, he will be overwhelmed, especially with a speedster like Gai and Jiraiya's agile moveset. Sakura will barely be able to handle Tsunade, but in the end I think that Tsunade will out best her.Actually, considering Itachi's reserves, Sakura could prove to be beneficial.
She's already been shown to transfer chakra to Obito, so she could do the same to Itachi who could then spam clones and Amaterasu.
Team Gai should have this