Tuncay started off the season brightly, his first league goal being the winner against Stoke City, in the third league game of the season. After a knee injury while playing for Turkey against Belgium in the World Cup Qualifiers in early September 2008, Tuncay was sidelined for five weeks. He returned to first team action against Blackburn Rovers on 10 October, and scored an overhead kick goal which was wrongly ruled out for offside. Tuncay scored his first brace in the Premier League in a 2–1 away win at Aston Villa on 9 November 2008. In December 2008, newspapers speculated that he was wanted by Chelsea in the January 2009 transfer window; Gareth Southgate laughed off the rumours suggesting that Chelsea could get him for such a small fee, saying that if he was even to start to consider selling him, then Chelsea's bid would have to be much higher. Tuncay scored two goals in as many games; during his side's 2–0 victories over both West Ham in the FA Cup and against Liverpool in the league, with the latter bringing an end to both Liverpool's 15-match unbeaten run, and Boro's 14-match winless run in the league. The win against West Ham takes Boro to their fourth Quarter Final in the FA Cup in four consecutive seasons. Against Tottenham in March, he had 2 goals again ruled out for offside, in a game which Tottenham defeated Boro 4–0. April 2009 saw Tuncay score Boro's quickest goal of the season, just 3 minutes into the game. The match, against Hull City, finished 3–1 to Middlesbrough in what was described as a "must-win game" by manager Gareth Southgate. In May 2009 he was named Boro's Player of the Year. On 16 May, in the penultimate game of the season, he scored a superb overhead kick goal against Aston Villa, which won him another BBC Goal of the Month award. In the vital game, an injury to captain Stewart Downing in the 23-minute meant that Tuncay took the captain's armband. This was the first time he has played as captain for Boro, and played a vital role in midfield. Despite Tuncay's efforts, Middlesbrough were relegated at the end of the 2008–09 season after suffering a 2–1 defeat away to West Ham. Middlesbrough had spent the whole second half of the season in the relegation zone. In the final game of the season Tuncay,