Goals against Blackpool, Ipswich Town and Watford followed but it was to be another frustrating season in front of goal for the striker who towards the latter stage of the campaign was used in a left midfield role. On 31 October 2009 he scored a hat-trick against Peterborough where the game finished 3–2. He was the first player to score a hat-trick at the Ricoh Arena. Eastwood was released by Coventry City when his contract ran out at the end of the 2011/2012 season. Return to Southend On 22 March 2012, Eastwood returned on loan to his former club Southend United until the end of the 2011–12 season. He made his second Southend debut on 24 March 2012 in a 1–0 defeat against Bristol Rovers at the Memorial Ground. He scored his first Southend United goal since his return in his second appearance in Southend 4–0 win against Cheltenham Town on 30 March 2012. At the end of the 2011–12 season Eastwood underwent surgery on a troublesome knee problem. On 12 July 2012, Eastwood signed a two-year contract to stay at Southend, following his release from relegated Coventry City. On 22 September 2012, Eastwood scored his first goal since his permanent return to Southend when he headed in from close range to score the winner in a 2–1 triumph over Exeter City. Eastwood returned for the start of pre-season training ahead of the 2013–14 season, looking thinner and sharper and started the season in his best form since 2005 after scoring 4 goals in consecutive games and claimed he was feeling as confident now as he was in his first spell with the club. Manager Phil Brown, claimed Eastwood was in the form of his career. Eastwood spent much of the 2013-2014 season as a squad player, playing in 30 League games, 19 as substitute. On 23 May 2014, Southend announced that Eastwood's contract was not to be renewed bringing an end to an association with Southend that brought 77 goals over two spells. The club in a statement said that Eastwood was a 'Southend legend'. International career His paternal grandmother was born in Wales, so Eastwood was eligible to play in the Welsh national team. He was selected for the squad for the international friendly against New Zealand in May 2007 and the crucial Euro 2008 qualifier against Czech Republic in June, however an existing back injury did not