In June 2002, Benfica signed him on a four-year deal, with Diogo Luís and Toni going in the other direction on loan deals.[6][7] From early on, Roland struggled with competition from Ricardo Rocha, and on occasions, Cabral.[8][9] He only made his debut on 3 November 2002 against Santa Clara,[10] but with the arrival of José Antonio Camacho, he began playing much more frequently, finishing the season with 14 appearances.[11] The following season, Cristiano was set to reunite with Jesualdo Ferreira at Braga, but the loan deal fell through.[12][13] Still, Roland started 8 league games in the first half of the season, until the arrival of Fyssas in January.[14] From then on, he became a bench player and never returned to the starting eleven.[15] In May, he added his second trophy in Portugal, after winning the 2003–04 Taça de Portugal.[16]