Trinidad fought Camacho, who had moved up in weight class, on January 29, 1994, in Las Vegas, Nevada. The bout went the distance, twelve rounds, ending Trinidad's streak of nine consecutive knockouts, but in the end he triumphed with a unanimous decision. In September 1994 began his next knockout streak with a fourth-round TKO over Luis Ramon Campas in Las Vegas. Over the next five years Trinidad would run his knockout string to ten in a row.
On February 20, 1999, Trinidad took on Pernell "Sweat Pea" Whitaker in New York City. Whitaker was also one of the most dominating boxers of the 1990s, first winning the World Boxing Council (WBC) lightweight crown in 1989. He unified the title in 1990 and held it until 1992 when he moved up in weight class to the welterweight division. He was WBC welterweight champion from 1993 to 1997. Now against Trinidad, Whitaker was attempting a comeback, of sorts, and hoping to capture the IBF welterweight title. But once again Trinidad was not to be denied. The fight lasted the full twelve rounds, with Trinidad winning by a unanimous decision. After a May tuneup bout against Hugo Pineda, Trinidad signed to fight boxing's "Golden Boy" of the 1990s—Oscar De La Hoya.
De La Hoya was another dominating boxer in the 1990s. A 1992 Olympic gold medallist, De La Hoya had defeated Whitaker for the WBC welterweight title in 1997; at the time of his fight with Trinidad, De La Hoya was undefeated in thirty-one bouts. The fight's victor would take the other's crown.
It was a classic fight between a power puncher (Trinidad) and a boxer (De La Hoya) when the two met on September 19, 1999 in Las Vegas. The fight was scheduled for twelve rounds. De La Hoya won most of the early rounds as he seemingly befuddled Trinidad. But Trinidad never lost heart. He won the final three rounds on stamina and power and took a majority decision—two judges voted for Tinidad and the third scored the fight even—to claim De La Hoya's WBC title as well as retain his own IBF title.
In his next victory, on March 3, 2000, against David Reid in Las Vegas, Trinidad won the WBA super welter-weight title. By the end of the year Trinidad had unified the super welterweight title with a TKO in the twelfth round over Fernando Vargas.