The popular party game, which involves contestants having to flip their cup over perfectly back onto a table after drinking from it, was comically enhanced on the late night show as Pine and Fallon performed the game while in wide, inflatable jumpsuits.
"Why is yours fatter?" the actor asked Fallon before the game commenced. "Well, I've been doing this longer," Fallon joked.
After a quick dance-off, Pine dispatched of Fallon in seconds hurriedly drinking and flipping over all six of his cups in record time making him the undeniable Inflatable Flip Cup champion.
Pine, who is currently promoting his latest film Star Trek Beyond, due in theaters July 22, discussed his recent Emmy nomination for Crackle series SuperMansion and getting to work alongside Jeff Bridges in upcoming drama Hell or High Water.
"Every wish you have about Jeff Bridges is absolutely true," Pine said before impersonating Bridges' laugh.