Midfielder Jon Challinor joined from Rushden for £15,000 in August 2008 and signed a two-year deal on the eve of the new season.

He came through the youth ranks at Rushden & Diamonds, starting out as a right-back, but left in search of regular first team football and had spells with Stamford, Kalamazoo Kingdom in the USA and Cambridge City before joining Aldershot in 2003.

He was a first team regular there for two seasons, scoring  21 goals in 78 Conference appearances, and when he was surprisingly released in 2005 he was snapped up by Exeter City, where he spent two equally successful years, making 87 league appearances and scoring 22 times, helping them  to help them reach the 2007 Conference Playoff Final where they lost to Morecambe.

Re-joining Rushden & Diamonds on a free transfer in the summer of 2007, he played in the first 45 league games of the season and only missed out on an 'ever-present' record when an injury meant he missed the final game of the season. He had spent the early part of the season in midfield, but when switched to play up front in late February 2008 he scored in four consecutive games.

A versatile player, Challinor played mainly in central midfield but also as a stand-in right-back. With the club reducing its playing budget this summer, Jon was transfer-listed and joined Forest Green on loan at the start of the season.