1. SERGIO MARTINEZ
The Puerto Rican promised the upset when he challenged WBC middleweight king, and undisputed division leader, Sergio Martinez in June 2014. Few believed him. The ageing Cotto was chasing a title in a weight class for which he was deemed too small, against an opponent presumed too big. But the veteran, under the watchful eyes of new trainer Freddie Roach, made a mockery of the consensus, and battered Martinez into defeat in 10 rounds.
2. ANTONIO MARGARITO II
Blood and controversy blotted Antonio Margarito’s 2008 brutal victory over Cotto. The villainous Mexican was caught wearing loaded gloves prior to his next bout; throwing his earlier achievements into question. The Puerto Rican was convinced his first career defeat had been a victim of foul play, and was determined to punish his rival in their 2011 New York return. He succeeded, extinguished Margarito’s primitive rage, turning him into a physical wreck inside 10 rounds. Revenge served.
3. ZAB JUDAH
Cotto’s arrival among the leading fighters in the sport, pound-for-pound, was confirmed with this thrilling thrashing of Zab Judah. The snazzy American had his moments, drawing blood from Cotto’s mouth and right eye, but the WBA welterweight champion bossed large parts of this June 2007 showdown. Judah could not cope, and was dropped in the ninth before being finished in round 11.