extra time until his sending off in the 116th minute for a second bookable offence, as the club won 5–4 in the penalty shootout following a 1–1 draw. After serving a one match suspension, Caldwell returned to the starting line–up against Doncaster Rovers on 22 November 2008 and helped Burnley keep a clean sheet, in a 0–0 draw. Once again, he received a straight red card after dragging Richie Wellens back inside the area, in a 2–1 loss against Doncaster Rovers on 28 December 2008. After serving a two match suspension, Caldwell returned to the starting line–up against Swansea City on 10 January 2009, as the club lost 2–0. It wasn't until on 21 March 2009 when Caldwell scored his second goal of the season, in a 2–1 win against Plymouth Argyle. He then helped the club reach the play–offs after beating Bristol City 4–0 in the last game of the season. Caldwell then helped Burnley beat Reading 3–0 in the semi–finals of the Football League Championship play-off to reach the final. The highlight of Caldwell's Burnley career was lifting the Football League Championship play-off trophy as captain after beating Sheffield United 1–0 to play in the Premier League next season. However, he expressed mixed emotions, due to his former club, Newcastle United, being relegated. At the end of the 2008–09 season, Caldwell made 57 starts throughout the season, as the Scottish international was a virtual ever-present in the Clarets back-line. However at the start of the 2009–10 season, Caldwell suffered a groin injury while on international duty and was sidelined for a month. After making a recovery, he returned to the substitute bench for a match against Tottenham Hotspur and didn't make a return on 3 October 2009, starting the whole game, in a 2–1 win against Birmingham City. Following his return, Caldwell regained his first team place, starting seven matches between 18 October 2009 and 20 December 2009. He scored his first goal for the club, scoring from a header, in a 1–1 draw against Aston Villa on 21 November 2009. In a follow–up match against West Ham United, Caldwell received a straight red card for "hauling down Zavon Hines", as Burnley lost 5–3. After serving a one match suspension, Caldwell returned to the starting line–up against Fulham on 12 December 2009, as the club drew 1–1. However during a 2–0 loss against Wolverhampton Wanderers on 20 December