Santa Rosa's hits continued with the album
Expresión, which included the single "Fulana" (What's her name) and in 2001 with the album
Romántico. He released
Viceversa in 2002, which became a "hit" in the Latin community in the United States and in all of
Latin-America. In addition, he has long played an important role in the career of his friend and protégé,
Víctor Manuelle, who Santa Rosa discovered. The two released a joint live album late in 2005,
Dos soneros, una historia. In 2006, he released
Directo al corazón, and in 2007 he carried out a concert acknowledged by the critics, in Plaza Colón at
Santo Domingo and released
Contraste with
Conteo regresivo being a major album hit. Furthermore, he performs alongside
Chucho Avellanet, a musical comedy club-act called,
Cantando y Contando, (
Singing & Telling Stories), throughout the island. On February 9, 2008, Santa Rosa participated in an event named "Concierto del amor" which was organized in the
Madison Square Garden. In June 2008, "Contraste" received
Gold and
Platinum certification from the
Recording Industry Association of America. The concert in Chile, on June 28, 2008, was Santa Rosa's first ever in said country. the event took place in the Caupolicán Theatre and was attended by approximately 8,000 fans. On July 5, 2008, Santa Rosa became the first salsa singer to perform at the
Palau de la Música in
Barcelona. The event was a Sold Out, filling the venue with an attendance of 2,000. Santa Rosa was selected to perform at the "Balón de Oro" award ceremony, the most important honor in Mexican football. Santa Rosa was selected to take part in "La Nueva Salsa", where he would perform along several young salsa artists. Santa Rosa has also contributed to improving Puerto Rico's public education system. He participated in Sapientis Week, an initiative sponsored by the non-profit
Sapientis which brings distinguished public figures into classrooms in order to raise the public's awareness of the education crisis in Puerto Rico. On July 17, 2010, he participated in the opening ceremony of the 2010 Central American and Caribbean Games. In 2017, Santa Rosa had the opportunity to contribute to
Lin-Manuel Miranda's single "
Almost Like Praying". The song featured various Latin artists and all proceeds benefit the
Hispanic Federation's Hurricane Relief Fund, helping those affected by the hurricane that hit Puerto Rico. In November 8, 2019, Gilberto Santa Rosa was the featured
singer on
Norberto Vélez's YouTube channel titled "Sesiones Desde La Loma Ep. 2". In July 25, 2025, Gilberto Santa Rosa performed alongside
Bad Bunny for his
No Me Quiero Ir de Aquí concert residency, performing "
Baile Inolvidable" and "La Agarro Bajando". ==Film==