As part of the West Indies' 2003 World Cup campaign, he was recalled to the Test team for the 2003 home series against Sri Lanka.

[3][4][1] He later picked up a career best 11 wickets for the Windies, again at Sabina Park, in the second and final match of the 2005 test series against Pakistan.

[5] In May 2008, Collymore joined Sussex as a Kolpak player in a one-year deal, replacing Australian allrounder Ryan Harris.

Collymore was a notable part of the Sussex team that won the 2010 Division 2 County Championship title, claiming 57 wickets at an average of 19.87 in what was eventually his last season with the side.

[8][9] In September 2010 Collymore joined Middlesex County Cricket Club in a two-year deal to replace fellow Barbadian Pedro Collins.