São Vicente, Cape Verde
Rolando was born in São Vicente, Cape Verde. After beginning his career in the youth ranks of lowly S.C. Campomaiorense, he finished his development with Lisbon's C.F. Os Belenenses, which he joined at the age of 18. In his Primeira Liga debut, on 28 August 2004, he played 90 minutes and scored a goal in a 3–0 home win against C.S. Marítimo.