joint top scorer with Billy Sharp in League One in 2005–06 with 23 goals. The following season, Eastwood scored his 50th goal for the club in the Championship opener game against Stoke City. It would prove to be a difficult season for the striker and despite scoring 11 goal in the Championship, Eastwood was unable to prevent relegation back to League One, however the highlight of the Shrimpers season came when Eastwood scored the only goal, a spectacular 30-yard free kick in front of the away fans in the North Stand, during the Football League Cup fourth round win against Manchester United on 7 November 2006 to put the holders out of the competition. Wolverhampton Wanderers Eastwood signed a four-year deal with Wolverhampton Wanderers in July 2007 after completing a £1.5m move from Southend. The striker started the 2007–08 season impressively, scoring his first goal for Wolves on his full debut in the League Cup first round win over Bradford City, and finishing the month with 4 goals to his name, earning him the Championship Player of the Month Award for August. However, his goals dried up in the following months and he was often on the substitutes' bench or left out of the squad completely, with Andy Keogh, Jay Bothroyd, Kevin Kyle and Sylvan Ebanks-Blake now ahead of him in the pecking order. He was close to a move away from Molineux to Coventry City in March 2008, but this collapsed at the last minute. He remained popular with many Wolves fans, who believed he had not been given a fair run of games, which caused a split between the fans towards the end of the season. He finished the campaign with just 3 goals in 10 league starts (35 appearances in total), prompting him to leave the club, with manager Mick McCarthy explaining, "It's nothing personal, but it hasn't worked out how either of us would have liked. He hasn't fitted into my team but he wants to play and will do well elsewhere. We wish him luck." Coventry City In July 2008, he joined fellow Championship club Coventry City in a four-year deal for a reported £1.2 million fee. Eastwood made his Coventry City debut against Norwich City on 9 August 2008, Coventry won the game 2–0. Eastwood scored his first goal for the Sky Blues a week later against Barnsley in a 2–1 win for Coventry.