Having acted as captain of Barnsley during much of the 2007–08 season when Paul Reid was out of the team, manager Simon Davey appointed Howard captain on a permanent basis in January 2008. He said it was a "massive honour" to captain a top-half Championship team, and appreciated the trust Davey and the club had in him. That season, Barnsley reached the semifinals of the FA Cup. In the fifth round, Howard scored a 93rd-minute winner to beat Liverpool 2–1 at Anfield. Barnsley eliminated Chelsea in the next round to progress to the semifinal, which they lost to Cardiff City. Howard was named in the PFA Championship Team of the Year.