January 2007, he was sent out on loan to Belgian club Royal Antwerp, to gain match experience. However, after just two games he suffered an injury, which ultimately sidelined him for the rest of the season, and he returned to his parent club in May 2007. In November 2007, Gray was loaned to Crewe Alexandra on a one-month deal to provide cover for the club's injured players. He made one appearance during his brief loan spell, playing 80 minutes in Crewe's 2–0 away defeat to Nottingham Forest. He returned to Manchester United in December that year, and spent the remainder of the 2007–08 season playing for the reserve side. Gray was to enjoy his first spell of first-team football during the 2008–09 campaign, with the player signing for Championship side Plymouth Argyle on loan in January 2009 until the remainder of the season. He made his Plymouth debut in a 3–1 away defeat to Arsenal in the FA Cup two days after signing, and went on to make 15 appearances in all competitions during his loan spell. Gray rejoined Plymouth for a second loan spell in September 2009, featuring regularly once again, making 12 league appearances for the club before returning to Old Trafford in December 2009 at the end of his loan agreement. Although both Plymouth and Manchester United discussed Gray's move to Home Park being made permanent in January 2010, no transfer materialised and the player remained at Manchester United, captaining the reserve side on a number of occasions during the latter stages of the 2009–10 season. Preston North End Gray's Manchester United contract expired at the end of the 2009–10 season, and although he was offered a one-year contract extension with the club, he opted to join Preston North End on a two-year contract on 16 July 2010. Gray started the 2010–11 season as a regular in Darren Ferguson's side, making his debut in a 2–0 home loss to Doncaster Rovers on the first day of the campaign. He was ever-present during the first three months of the season, before suffering an injury in November 2010 that ultimately ruled him out of first-team action for three months. He returned to the first-team in a 1–0 away defeat to Hull City on 12 February 2011, although would suffer an even bigger injury setback a month later after breaking his leg in a 1–1 draw against Norwich City at