Jon Challinor is an attacking midfielder, who often plays 'in the hole' between midfield and attack. He joined Rushden & Diamonds from Exeter City prior to the start of the 2007 / 08 season. At the Grecians, Jon started 36 games in the 2006 / 07 season, scoring 10 goals to help Exeter reach the Conference Playoff Final. With 41 games and 12 goals in the 2005/06 season, Jon was an important part of Exeter's fortunes in the Conference.

A regular for Aldershot in the two seasons before his move to Exeter, Jon was surprisingly released by the Shots, despite 21 goals and 74 appearances.

Challinor has also had spells at St Albans, Cambridge City and Stamford, whom he joined from Nene Park in search of regular football. Jon also spent a short stint in the USA for Kalamazoo Kingdom.

Initially part of the Rushden & Diamonds youth team, Jon struggled to find regular football during this period, as Brian Talbot brought in Shaun Carey and Ritchie Hanlon in pursuit of promotion to the Football League.

In his first season back with Rushden & Diamonds, Challinor appeared in the first 45 league games of the season, narrowly missing out on an "ever-present" record when an injury in the game against Grays meant he missed the final game of the season against his old club Aldershot Town.  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. 

Challinor controls the ball