2008–09 season, and was voted Sheffield United Player of the Year at the end of the season. Kilgallon started the 2009–10 season as a regular starter once more, but with his contract due to expire the following summer, discussions over a new contract with the club were unsuccessful. At the turn of the year, Kilgallon announced that he intended to see out the remainder of his contract and rejected the opportunity to open transfer talk with Premier League club Burnley. Sunderland Kilgallon signed for Premier League club Sunderland on 21 January 2010 on a three-and-a-half-year contract for an undisclosed fee. He made his debut six days later, starting in a 2–0 loss away to Everton. Kilgallon struggled to make an impact during Sunderland's winless run until a man-of-the-match performance against Hull City on 24 April 2010, his first start in months. On 19 August 2010, Kilgallon joined Championship club Middlesbrough on loan for the 2010–11 season. After a man-of-the-match performance at left-back against Sheffield United, his loan was cut short by injury. On 12 January 2011, Kilgallon joined another Championship club, Doncaster Rovers, on loan for the rest of the 2010–11 season. After his loan return from Doncaster Rovers, he was not given a squad number for the 2011–12 Premier League. However, after Steve Bruce was dismissed in November 2011, Kilgallon was given a squad number by new manager Martin O'Neill. He returned to the first-team squad as an unused substitute during Sunderland's 2–1 victory over Blackburn Rovers on 11 December 2011. On 1 January 2012, Kilgallon made his first Sunderland appearance since May 2010, coming on as a 26th-minute substitute for the injured Wes Brown against Manchester City. Kilgallon helped keep a clean sheet as Sunderland beat the league leaders 1–0. Two days later, he made his first Sunderland start since May 2010, playing alongside John O'Shea in central defence in a 4–1 away win against Wigan Athletic. He suffered an ankle injury during a 1–0 away defeat against Chelsea on 15 January 2012 and did not reappear until 31 March, starting in an away match against Manchester City. He was substituted in the 81st minute with Sunderland winning 3–1, before the team conceded twice to draw 3–3. During the 2012–13 season, Kilgallon failed to appear in the league until starting in a 0–0 home draw to Queens Park Rangers on 27 November 2012. After playing in Sunderland's 3–0