PFC Litex Lovech
Cuéllar made his official first team début on 18 September in the 3–1 UEFA Cup first round victory against PFC Litex Lovech in Bulgaria. He made his first league appearance for Aston Villa in the West Midlands Derby match against West Bromwich Albion on 21 September. Cuéllar came on as a late substitute in a match which Aston Villa won 2–1. His first league start came against Portsmouth on 19 October 2008, where he however operated as a right back. Most of Cuéllar's league appearances during his first season were in that position, due to the good form in the central partnership of Curtis Davies and Martin Laursen.