Terence Crawford‘s resume is indeed a gold standard for every boxer. 41 fights, 41 opponents, and not a single loss or draw. Furthermore, if everything goes according to plan, there is a good chance he might join the elite list of boxers retiring with an undefeated record. However, in front of him stands possibly his biggest challenge: Canelo Alvarez. The Mexican juggernaut might be the only one who could put a blemish on Bud’s perfect record and ruin his dream farewell. The two-division undisputed champion will not only face one of the best, but will do it at 168 lbs, two weight divisions higher than where he is at now. However, this is not the first time that Terence Crawford has faced unprecedented odds.The 37-year-old has defeated greats like Errol Spence Jr., Shawn Porter, Amir Khan, Viktor Postol, Kell Brook, and Israil Madrimov. Yet, in a shocking twist, none of these formidable opponents stand as his greatest test. And who might that be? Let’s find out.Olympic gold medalist who kept Terence Crawford on his toesDuring his first Australian tour, Terence Crawford sat down with Jai McAllister from Bondi Boxing Club in Sydney to interact with the fans. During the event, a young fan named Theodore asked, “What’s your toughest fight and what weight division was it?” Without wasting a second, the Nebraskan replied, “My toughest fight was, uh, Gamboa. It was at the lightweight division.” Bud fought Yuriorkis Gamboa almost a decade ago in 2014 while defending his WBO lightweight title. The 2004 Athens Olympics gold medalist was on a tear at the time was undefeated with 18 wins.ROUND NINE IN FULL.Terence Crawford vs Yuriorkis Gamboa pic.twitter.com/Sf7QsfDbGd— Top Rank Boxing (@trboxing) February 26, 2025It was supposed to be Terence Crawford’s first major test on the big stages. And as things stand, the Omaha native still considers it his biggest challenge yet. “Gamboa was fast, he was experienced, he was explosive. I got down in that fight and I just had to stay focused, and, you know, keep my poise and stick to the game plan,” he concluded.While Terence Crawford defeated the former IBF featherweight champion in the ninth round via a TKO, things were not that smooth. The Cuban dominated Bud during the initial stages of the match, especially stunning the two-division undisputed champion in the fourth round. The tables turned in the fifth round when Terence Crawford knocked the 2004 Olympic gold medalist down.Gamboa might have lost the fight, but he earned Terence Crawford’s lifelong respect for his efforts. As this is not the first time that the Nebraskan has given the Cuban his flowers. After his unanimous decision victory against Israil Madrimov last year, where the Uzbekistan native took him to distance, Crawford still claimed Gamboa to be his toughest challenge.However, after countless triumphs, it seems like Terence Crawford might finally hit the wall when he faces Canelo Alvarez on September 13, at least that is what the Mexicans’ camp thinks.A confirmed knockout win for Canelo AlvarezUnsurprisingly, ever since this blockbuster bout was announced, the boxing world has been favoring the Mexican juggernaut massively. That all changed after Cinnamon’s fight against William Scull. Despite reclaiming his undisputed super middleweight crown, Canelo’s performance was far from desired. He threw just 152 punches in all 12 rounds, with the Cuban playing defense the entire time. The snooze fest gave confidence to Terence Crawford fans who now believe a victory may not be too difficult.However, despite the lackluster performance, it has not hampered Canelo and his camp at all. In a recent interview with Elie Seckbach of ES News, Eddy Reynoso, long-time coach of Cinnamon, was asked to predict the September 12 showdown. Without mincing his words, Reynoso replied, “Whatever round—they’re going to win by knockout,” in Spanish.Seckbach further pressed, “Crawford is a good fighter, but Canelo is the best,” adding fuel to Reynoso’s confidence. The coach doubled down and stated, “Crawford’s a great fighter. But that day, he’s facing Canelo.” Meaning? Terence Crawford may have bitten off more than he can chew, and no matter what he brings, it won’t be enough to take down Canelo.Do you think Terence Crawford has a chance against Canelo Alvarez? Drop your predictions down below, and also mention your favorite match of Crawford.The post Terence Crawford Reveals His ‘Toughest Fight’ Before Facing Canelo Alvarez appeared first on EssentiallySports.