Born in Wellington, Telford, Shropshire, Proudlock began his career as a trainee with Wolverhampton Wanderers in August 1998. He had a loan spell at Scottish side Clyde at the start of the 2000–01 season to gain first team experience. There, he scored a hat trick on his professional debut on 5 August 2000 against last seasons Scottish 1st Division champions Falkirk in a 3–1 win at Broadwood. He scored five times in six games for Clyde and was named Scottish Division One player of the month for August 2000. He was recalled by Wolves and offered a new contract until 2003. He became a regular starter for Wolves throughout that season, which he ended as their top goalscorer with 11 goals.