According to Soccer America, Chicago Fire goalkeeper Matt Pickens joined Norwich City on trial in January 2008.

Pickens played college soccer for Southwest Missouri State University from 2000 to 2003, as well as playing for the Chicago Fire Reserves.

Upon graduating, Pickens was drafted 19th overall in the 2004 MLS SuperDraft by the Fire. He was not able, however, to break through a deep lineup of Fire goalkeepers, which initially included Henry Ring and D.J. Countess, and later Zach Thornton. He was loaned out for much of the year to the A-League Virginia Beach Mariners, where he played 290 minutes, allowing only 3 goals.

During the latter half of 2006, after an injury to Zach Thornton, Pickens started in goal for the Fire. Pickens has been the Chicago Fire's starting goalkeeper for the 2007 season and has become a fan favorite nicknamed "Slim Pickens" by the Section 8 supporters group

Upon leaving Norwich, Matt trialled with Preston before joining QPR on 7th February 2008 on a short term contract until the end of the 2007/8 season. This was not renewed

In the early part of 2009, Matt signed for he Colorado Rapids.