At West Ham, Eastwood played in the same youth team as Jermain Defoe, Anton Ferdinand, and Glen Johnson but was not considered good enough by manager Glenn Roeder and was released by the Hammers in May 2003.

[8] Eastwood joined Southend on a permanent basis in November 2004 for an undisclosed fee in a three-year deal from Grays.

[11] He scored twice at Swansea City on 29 April 2006 to earn Southend United a 2–2 draw, a result which sealed promotion to the Football League Championship.

[14] It would prove to be a difficult season for the striker and despite scoring 11 goal in the Championship,[2] 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.

[17] 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 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.

"[19] In July 2008, he joined fellow Championship club Coventry City in a four-year deal for a reported £1.2 million fee.

On 12 July 2012, Eastwood signed a two-year contract to stay at Southend, following his release from relegated Coventry City.

[33] Eastwood was born to a Romanichal family in Epsom, Surrey and was often seen exercising his horse on the A127 road in Essex on the morning of a match day when playing for Southend United.

[35] Eastwood and his family were told in November 2006 that the decision of Basildon Council would not be upheld by the Government and he was free to stay there for at least the next five years.

[36] Eastwood was fined by magistrates in July 2009, after he had been caught fly-tipping rubbish which included an electricity bill and bank statements containing his name.