Over the next several years, Pacquiao engaged in a series of high-profile fights, winning the World Boxing Association (WBA) and IBF featherweight titles, the WBC and The Ring’s junior lightweight titles, and the WBC lightweight title. His rise was aided by American trainer Freddie Roach, who gradually transformed the left-handed slugger into a multifaceted boxer without detracting from his natural aggression or punching power. He was the Boxing Writers Association of America and The Ring’s Fighter of the Year in 2006 and 2008.

On December 6, 2008, Pacquiao faced and thrashed American boxing star Oscar De La Hoya in a celebrated nontitle welterweight bout in Las Vegas. By then Pacquiao had become a complete fighter, combining excellent footwork, blazing speed, and a vastly improved defense, and he was widely considered, pound for pound, the world’s finest boxer. In addition, Pacquiao’s popularity as a pay-per-view (PPV) boxing attraction had increased steadily since 2002, but the match with De La Hoya was his breakthrough as a global phenomenon. The fight sold approximately 1.25 million buys, generating roughly $70 million in PPV revenue, one of the largest PPV grosses in history for a nonheavyweight bout.

Manny Pacquiao (right) and Floyd Mayweather, Jr., in their 2015 welterweight bout

On May 2, 2009, Pacquiao won The Ring’s junior welterweight championship (his sixth weight class as a champion and his ninth as a professional boxer) with a spectacular one-punch second-round knockout of England’s Ricky Hatton. On November 14 he added another championship belt—in a record seventh weight class—when he defeated Miguel Cotto of Puerto Rico in 12 rounds to take the World Boxing Organization (WBO) welterweight title. Pacquiao defended that title on March 13, 2010, in Arlington, Texas, by defeating Ghanaian boxer Joshua Clottey in 12 rounds. He increased his weight-class titles record to eight when, on November 13, 2010, he soundly defeated WBC super welterweight champion Antonio Margarito, who outweighed Pacquiao by 17 pounds at the time of the fight.

Pacquiao had a 15-bout winning streak that came to an abrupt end in June 2012 when he lost his WBO welterweight title to Timothy Bradley in a controversial split decision. In December 2012 he lost a non-title bout to Juan Manuel Márquez—against whom Pacquiao had previously won two fights and drawn another—when he was knocked out in the sixth round. It was the first time Pacquiao had been knocked out since Singsurat did so in 1999. He regained the WBO welterweight belt in April 2014 by beating Bradley in a unanimous decision. Pacquiao’s next major bout was against the undefeated Floyd Mayweather in May 2015, a much-anticipated contest that the two fighters’ camps had been negotiating on and off for more than six years. In that event, Pacquiao was unable to mount an effective offense against Mayweather, who was arguably the greatest defensive fighter of his generation, and he lost by unanimous decision. After having won a decision over Bradley on April 9, 2016, he retired from boxing for four months before announcing another fight. On July 2, 2017, he lost a decision and the WBO welterweight title to Australia’s Jeff Horn. Pacquiao bounced back to capture the WBA welterweight title in a victory over Lucas Matthysse on July 15, 2018. On July 20, 2019, he won a split decision over the previously undefeated Keith Thurman to take the WBA super welterweight belt and become, at 40 years old, the oldest welterweight champion in boxing history.