The key being 'under Max'? You cannot sensibly start both even in a 442 as they are too similar.
The forward going RB 'Max' has used include Dani Alves and MDS (

) . Dani Alves was similarly deployed further forward many times, while Barza (a true CB if god ever created one) was playing RB position for us. As I said Cuadrado and Cancelo play the same style, almost the same position and will overlap too often. Would Allegri change our system, I hope so - but won't include both.
BTW while Candreva is different, I think his problems are similar in Inter with Cancelo. He will be better suited to a more defensive RB and a 442.
Ergo - one of them yes, both NOT a chance.