Roldan, born in the Cordoba province, made his professional debut December 8, 1978 in San Francisco, Argentina, against Jorge Servin, winning by knockout in round one. His first four wins all came by first round knockouts.
On May 11, 1979, Roldan fought the full distance in one of his bouts for the first time, when rival Hugo Obregon went ten rounds with him. Roldan won the fight on points. On September 21, 1979, Juan Carlos Borgado became the first boxer to defeat Roldan, winning a ten round decision over Roldan.
Out of his next eighteen bouts, he won seventeen and drew (tied) once. Then, he challenged Jacinto Fernandez on March 13, 1981, for the Argentine Middleweight title. He won the national title with a twelve round decision over Fernandez. In his next fight, he beat Jose Maria Flores Burlon, a boxer who would later challenge Carlos De Leon for the world's Cruiserweight title. Roldan won six more fights and drew one before challenging Jose Maria's brother, Carlos Flores Burlon for the South American Middleweight title, on February 12, 1982. He won the title with a second round knockout.
Before 1982 was over, he would see more action, retaining his Argentine Middleweight title with a first round knockout of Marcos Perez, but losing on a disqualification in three rounds to Ricardo Arce. In an immediate rematch, Roldan put his Argentine title on the line and this time, he avenged his defeat to Arce with a two round knockout win. After five more wins in a row, he fought Juan Carlos Peralta, with the fight resulting in a three round no contest.
On May 27, 1983, Roldan made his international debut, with a 10 round decision over Teddy Mann in Rhode Island, USA. After retaining his Argentine title twice more, he was faced, on November 10, 1983, with one of the top rated Middleweights of the time, Frank The Animal Fletcher, at the undercard of the high-profile, Marvin Hagler-Roberto Duran world title fight in Las Vegas, Nevada. Roldan dropped Fletcher twice on his way to a sixth round knockout victory.
After this win, Roldan was ranked number 1 by the major boxing organizations, and many fans began to speculate as to what would happen if he and Hagler met. The contracts for the fight were signed, and the fight finally came off on March 30, 1984. Roldan in this fight had the moment that probably defines his career better. Seconds into round one, as Hagler was bending to duck a Roldan punch, Roldan struck him in the back of the head, and Hagler went to the floor. Referee Tony Perez officially ruled it a knockdown, making Roldan the first man to drop Hagler. This was a controversial knockdown, however, many fans, magazines and websites have tirelessly claimed that the knockdown was actually a slip and not a knockdown. Hagler got up and proceeded to beat Roldan by a ten round technical knockout, and Roldan announced his retirement from boxing in October of that year. Roldan remained the only guy to officially score a knockdown against Hagler.
In 1986, he reconsidered his decision and made a comeback. He won twelve bouts in a row, including one over James Kinchen, before he challenged for a world title again. On October 29, 1987, at Las Vegas, Thomas Hearns became the first boxer to win world titles in four different divisions when he beat Roldan in four rounds by knockout, but not before Roldan had Hearns in trouble in round three.
On September 16, 1988, Roldan beat former world Middleweight champion Hugo Corro by a knockout in round one in Mar del Plata, securing a third world title shot, against Michael Nunn, on November 4 of that year. Roldan lost what turned out to be his last fight, by a knockout in round eight.
Roldan retired with a record of 67 wins, 5 losses, 2 draws and one no contest, 47 of his wins being by knockout.