Orient before returning to Premier League club Reading, making Eastwood the only goalkeeper at Portsmouth, and securing his first-team place. Just after Andersen's departure, former Swindon Town goalkeeper Phil Smith was signed, initially as back-up for Eastwood. Eastwood's position was under threat, when former Portsmouth goalkeeper Alan Knight (famous for the most appearances for a Portsmouth player) came in as goalkeeper coach (after the departure of John Keeley). Knight backed Eastwood, and on 2 March 2013 Pompey won their first match in over four months (23 matches), a 2–1 win at Crewe Alexandra, Eastwood's first win as a Portsmouth player. In the next month he kept three clean sheets in six matches, against Bury, Preston North End and Tranmere Rovers. Following Portsmouth's relegation, Eastwood said he was determined to stay at the club for the next season. He was offered a new contract with the club. Blackburn Rovers Eastwood rejected Portsmouth's offer and on 13 May 2013 agreed a deal in principle to join Championship club Blackburn Rovers. He made his debut for the club on 7 August 2013 in a first round League Cup tie against Carlisle United, which Blackburn lost on penalties after a 3–3 draw. In December he displaced Jake Kean as first-choice goalkeeper, making his Championship debut for the club on 7 December 2013 in an away match against Queens Park Rangers, putting in an impressive performance and keeping a clean sheet in a 0–0 draw. After seven matches as first choice, Eastwood returned to being back-up as Paul Robinson returned from injury and reclaimed his number one spot. On 28 February 2014, Eastwood signed a new contract until the summer of 2016. Oxford United In June 2016, Eastwood signed for Oxford United for the second time, on a one-year contract. He was given the number 1 jersey and played every minute of all 62 first-team matches in 2016–17, including the 2017 EFL Trophy Final at Wembley Stadium. He signed a two-year contract extension in February 2017, and was voted the Supporters' and Players' Player of the Year at the club's end-of-season awards. The following season he was again ever-present in league fixtures, though he was rested for a couple of EFL Trophy games. Eastwood signed a new three-year contract with Oxford in May 2018. Eastwood suffered a broken finger during the warm-up of the second League One fixture of the 2018–19 season on 11 August