Matthew Rees was a product of the Pontypridd Under-21 Academy from the 2000–01 season. His nickname at Sardis Road was "Smiler". Rees made one substitute appearance for the side in the 2001–02 Celtic League, along with three appearances as a replacement in the 2001–02 European Challenge Cup. In the following season, Rees played in three 2002–03 Celtic League games, starting in two, and made three appearances in the 2002–03 European Challenge Cup, two of these coming from the bench.