Russell Penn signed for the Harriers just before the start of the 05-06 season after being released from his previous club, Scunthorpe. He spent three years as a trainee there but never made an appearance for them.
He previously played for the Harriers when he was a member of their youth squad in 2002 but then left to join Scunthorpe. On his return to Aggborough in July 2005 he went out on loan to Alvechurch for a month then once back he went on to stake a regular starting place in the side.
He came to the notice of Paul Fairclough when he was in charge of the England C Team and became a regular international standard player for many years. In 2009 he was given the honour of England C Player of the Year.
In 2008 he was a target for both Walsall and Peterborough with talk of him going to either club for a six figure fee but nothing ever came of it. He did finally leave Aggborough to join Burton Albion in July 2009 for a fee thought to be in the region of £50,000. Considerably less than his supposed worth a year earlier.