Whittingham began the 2007–08 season on the bench. By mid-November Cardiff found themselves just above the relegation zone; this prompted a minor reshuffle from boss Dave Jones that involved Chris Gunter and Whittingham returning to the starting line-up. Whittingham's recall saw him moved to an unfamiliar role on the right side of midfield, but he soon settled into the role and started the majority of the remaining matches of the season, as well as being the team's top scorer (with three goals) during their FA Cup run. That run saw him score in matches against Chasetown, Wolverhampton Wanderers and Middlesbrough, before Cardiff eventually lost 1–0 to Portsmouth in the final.