2009. After 28 appearances (22 in the league) he returned to the Galpharm on 31 December, after Bradford manager Stuart McCall said he needed a more experienced goalkeeper at the club. Oxford United On 4 June 2010, Eastwood signed a two-year contract with Oxford United, newly promoted to League Two. However, Eastwood was second-choice goalkeeper behind ever-present Ryan Clarke, who made 50 appearances in the 2010–11 season. After one season at Oxford, having failed to make a first-team appearance, Eastwood was released in May 2011 despite having a year left on his contract. F.C Halifax Town On 21 June, Eastwood signed a one-year contract with Conference North club F.C. Halifax Town. On 13 August he made his debut, against Corby Town. He won the competition for first-team place against Phil Senior, making 43 appearances (41 in the league), only missing three league matches. However, at the end of the season he opted to sign a contract with local side Bradford Park Avenue instead of signing again for Halifax. Portsmouth On 8 July 2012, Eastwood agreed a contract with Conference North club Bradford Park Avenue. However, just five days later, after Eastwood chose to take a trial with Portsmouth, his contract with Bradford was rescinded, the club stating that it would not stand in his way. After featuring in all Portsmouth's preseason matches, Eastwood joined Pompey on 13 August 2012, on non-contract terms, one day ahead of their League Cup tie against Plymouth Argyle, in which he made his debut. On the eve of the new league season, Portsmouth signed their entire new squad, including signing Mikkel Andersen from Reading on loan. Andersen secured first place in the team, meaning Eastwood was on the bench. Eastwood played his second match on 9 October, in a Football League Trophy second round match against Wycombe Wanderers; the club failed to progress after losing 3–1. However, Eastwood managed to save a penalty although the rebound was scored by Wycombe's Dean Morgan. Due to limited playing time, Eastwood was the main goalkeeper for Portsmouth's development squad. He made his third first-team appearance in a first round FA Cup match against Notts County, on 3 November. On the following Tuesday, he made his league debut at Fratton Park against Brentford; Pompey lost the League One fixture 1–0. On 20 November 2012, first-choice goalkeeper Andersen made his last appearance for Portsmouth in a 2–3 defeat to Leyton