After beginning his career in the youth ranks of lowly S.C. Campomaiorense, Rolando finished his football formation with Lisbon's C.F. Os Belenenses, which he joined at nearly 18. In his first division debut, on 28 August 2004, he played 90 minutes and scored a goal in a 3–0 home win against C.S. Marítimo; he went on to become an essential defensive figure onwards, appearing in all 30 matches in 2007–08, as the club finished in eighth place.
On 15 April 2008, F.C. Porto confirmed that Rolando had agreed to part ways with Belenenses and join them on a four-year contract. In his first season, he quickly beat competition from veteran Pedro Emanuel, partnering Bruno Alves in the centre.
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