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On June 28, 2014 Gamboa faced off against undefeated WBO titlist Terence Crawford on HBO boxing after dark. Gamboa got off to a hot start, winning the first 4 rounds and using his superior foot speed and hand speed but was caught and dropped by a left hook in the 5th round.

Gamboa continued to fight back but was dropped again in the 8th and finally was stopped in the 9th round after two knockdowns and a huge right hook by Crawford. “We were just two warriors in the ring trying to get the victory, and he won.” stated Gamboa after the bout. This was Gamboa’s first loss as a professional, ending his undefeated streak.