weston signed for football league championship team scunthorpe united on loan, in march 2008. in august 2008, weston joined gillingham, initially on a one-month loan, before signing a two-year contract. he said "when the chance came to go to gillingham i grabbed it. ..being from the area, i knew the club, knew the set-up was good. it was the chance to move back to where my family is, and to play regular games". he made his gillingham debut away to bournemouth on 9 august 2008, and scored his first goal for the club on 28 december 2008 against wycombe wanderers.