After one appearance in an independent company in Puerto Rico where he worked as "El Pelotero", Cotto debuted in the International Wrestling Association in 2000.
On June 11, 2005, Cotto defeated Shane Sewell and Ricky Banderas in a three-way, in the process winning the IWA World Heavyweight Championship for the first time.
They arrived as "La Rabia", after one week in WWC, Cotto decided to return to the IWA, citing that he felt uncomfortable with the promotion's work ethics and feel.
[2] Both wrestlers continued performing, with Cotto scoring a pinfall victory after reverting a finisher and receiving the count from a substitute referee.
[2] Late 2009, Chicano and his partners "Los Fugitivos de la Calle" (El Niche, Lynx, El Cuervo) appeared on a television segment of WWC program "Las Superestrellas de la Lucha Libre" making an alliance with his old friend and former member of "Lucha Libre 101" Bryan Madness.
Chicano and Bryan won the WWC Tag Team Champion in Euphoria 2010 by pinfall over Thunder & Lightning with the intervention of El Cuervo.
On November 7, 2010, Cotto debuted in AAA as a masked character known as "El Ilegal", being booked to win a six-man tag team match, alongside Damián 666 and Halloween by applying a new finishing move.
[3] His entrance to the company was explained in a storyline, where he was brought in by Dorian Roldán Peña to join La Sociedad, a major faction trying to take over the promotion.
Cotto continued to feud for the tag team championships, but once the opportunity took place, he was removed, in order to introduce Savio Vega's student, Diego de Jesús.
He was initially awarded the Intercontinental belt and Angel's undefeated record, but the result was revoked due to external interference from a second masked "Illegal" and an unclean pin.
At Clash of the Titans, Cotto lost the EWO World Championship, losing to a masked wrestler only known as "Bonecrusher", whom he had defeated to win this belt and had since gained the IWA Undisputed Heavyweight Champion.
On May 26, 2012, Pérez made a face turn when Rondón insulted his father, which resulted in the entirety of Zona 101, led by Cotto, joining him and becoming part of Team IWA.
[16] He joined the municipal gymnasium of Aguas Buenas, where he began training along Efraín Román, Armando Alamo, Jonuel Tapia and one of his cousins, Abner Cotto.
[16] Cotto made his amateur debut on September 28, 2012, defeating his opponent by RSC after 30 seconds of the first round, also earning the recognition of "Most Spectacular Fight" of the night.
[24] On August 31, 2013, he won a disqualification after his opponent, Jimmy Suárez, ignored multiple warning following a series of rabbit punches, prompting referee Luis Pabón to stop the contest.
[30] This result lead to several changes in Cotto's career, who moved to the Villa Fontana Gym in Carolina, Puerto Rico where he trained under Gerardo Sánchez Jr., dropping 35 pounds and working on his technique.
[30] Cotto was frustrated by the result, arguing that he was hit with several rabbit punches and that referee Ramón Peña failed to notice them, immediately beginning the negotiations for a third fight between them.
[31][32] Colón Sr., who accompanied him to the ring along Juan and Dennis Rivera, argued that the sudden weight loss had in fact affected his performance, but the finish was described as "controversial" in the media.