Pacquiao had a chance to give Mayweather the lone loss of his career in 2015 but fell short in a blockbuster fight that resulted in a unanimous decision loss for the Filipino legend. Pacquiao is confident the second time will be the charm in what he’s billing as the most important fight of his Hall of Fame career.

In a fantasy fight, however, Pacquiao believes Mayweather would have already suffered defeat against the switch-hitting Terence Crawford if they were both pitted against each other.

“I think Crawford beats Mayweather if they both fought in their prime,” Pacquiao said on Monday's episode of “Inside The Ring” on DAZN. “He has the advantage as a southpaw. I saw Crawford as a southpaw; he mastered it. He knows how to handle his advantage, to maximize his advantage, against an orthodox fighter.”

Mayweather (50-0, 27 KOs) was a five-division champion in his Hall of Fame career, winning crowns across 130, 135, 140, 147 and 154 pounds and beating the best fighters of his generation before retiring in 2017.

Crawford (42-0, 31 KOs) retired as a five-division champion (three-division undisputed) in December after stepping up two weight classes in September to beat Canelo Alvarez for the undisputed super middleweight title in a career-best victory.

“Man, listen. That's the GOAT. [Mayweather is] one of the GOATs,” Crawford said shortly after beating the Mexican superstar. “I have nothing but the utmost respect for Mayweather. I would never compare myself to Mayweather. He's the greatest of his era, and I'm the greatest of my era.

"I don't understand why, especially our people, hate on Mayweather so much. He made so much history for us. He paved the way for me to be where I'm at. He motivated me in so many ways outside the ring with work ethic, hard work, dedication, that I can't even say.

"I don't know why a lot of people, well most people, always try to tarnish his career or want me to be like, 'I'll knock Mayweather out' or always try to compare us.”

Mayweather and Crawford's paths didn't cross during their respective careers, as they ended up being the greatest fighters of their eras.

Mayweather, who is 10 years older than Crawford, closed the book on his professional career at welterweight with a stoppage victory against Conor McGregor in August 2017, just days after Crawford became the junior welterweight champion. Crawford didn’t move up to welterweight until June 2018, when he captured the WBO belt with a ninth-round stoppage of Jeff Horn, who controversially beat Pacquiao the year before.

Crawford and Pacquiao could have fought each other, too, as they were both under contract with Top Rank for nearly a decade. But promoter Bob Arum admitted in 2019 to killing the fight because he feared Crawford would deliver a beating on Pacquiao that would have resulted in “serious disability for Manny.”

As for some other fantasy fights featuring fighters he shared the ring with, here’s how Pacquiao made his predictions on ITR.

Pacquiao also shared his Mount Rushmore of boxing, which included himself, Muhammad Ali, Sugar Ray Leonard and Julio Cesar Chavez.

Manouk Akopyan is The Ring’s lead writer. Follow him on X and Instagram: @ManoukAkopyan.