He had a good run in the team and scored important goals against Everton, Arsenal and Sheffield United,[3] before leaving on loan in February 1994 to join Wolverhampton Wanderers; this meant he missed out on Villa's victory in the 1994 Football League Cup final.
He scored eight goals in 13 Division One appearances for Wolves, although it wasn't enough for the Molineux side to reach the playoffs.
At Portsmouth during his loan spell his seven goals in nine matches helped the club avoid relegation to the third tier.
[7] This was the second time that Whittingham had been denied in an FA Cup semi-final by the Merseyside team, having lost in a penalty shootout to Liverpool whilst at Portsmouth in 1992.
Whittingham later went on to become player-manager of Newport (IOW), but left them in May 2005 when the club ran into financial difficulties.
He returned to management at AFC Newbury but when that club suffered financial difficulties and the loss of their ground, Whittingham left in June 2006.