Jamie McGuinness joined Rushden & Diamonds prior to the start of the 2008 / 09 season. The right-sided midfield player joined as an eighteen year-old free agent from Luton Town on a deal until the end of that season.

Jamie began his career at Luton, most playing on the right-hand side of midfield, and also had a brief loan spell at Aldershot Town last season. He was released by the Hatters at the end of their 2007/08 campaign, following the end of his Scholarship with the Club.

Jamie appeared for the Diamonds in the second half of their 7-0 victory over Halstead Town on Friday 11^th July 2008 and was signed to give Garry Hill more options in midfield as he prepared the squad for the first league fixture of the 2008 / 09 season at Eastbourne Borough.