Kyle's career started at the Terras, and he played numerous games for the Reserves side. In July 2003, then Premier League, Southampton spotted young Critchell plying his trade in the reserves team, and had soon signed him up to the Saints academy. During his first two years with Southampton, Kyle had featured regularly for the youth team, and had forced his way into their reserve team.

However, in the FA Youth Cup semi-final Critchell suffered a broken ankle and missed most of the next season with a cruciate ligament injury. After a spell on loan at Torquay, he moved to Chesterfield where he played ten games for the League One outfit before being struck with another injury. He was released at the end of the season.

Critchell returned to Weymouth to train in preparation of the forthcoming 2007/08 season, but eventually signed a contract to stay with his hometown club. He was a key figure in Jason Tindall's and John Hollins side throughout the campaign, and his never say die attitude helped keep the Terras in the Conference.

In the close season, recently relegated Wrexham were interested in the Welsh international, and finally signed Kyle in late June 2008. Unfortunately, an ankle injury kept him on the sidelines for four months. After recovering he spent the remainder of the season on loan at York City and Weymouth.

Kyle is sure to be a key member of Matty Hale's squad for the upcoming season, and the fans are extremely happy to see Critch back at the club.