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On 3 February 2015, Ashdown signed for Oxford United until the end of the season. He made his first-team debut, keeping a clean sheet, in a League Two match at AFC Wimbledon on 11 April 2015 that finished 0–0.

After being released by Leeds United, Ashdown joined Crawley Town on a contract until the end of December 2014.

Ashdown made his debut on 16 September 2014, in a 0–0 draw against Doncaster Rovers, keeping a clean sheet. Ashdown managed to beat off competition from Brian Jensen as first-choice goalkeeper. However, he was later criticised for a slow start at the club, despite being man of the match in a 1–1 draw against Crewe on 1 November 2014. In late November he was left out of the squad in favour of Lewis Price.

Ashdown endorses goalkeeping gloves made by The One Glove Company, who are donating proceeds to the charity Jack's First Steps. The charity partnership first launched on 16 December 2014 with the release of the "Pulse" goalkeeper glove.

Ashdown made his debut for Leeds on 28 August in a League Cup match against Oxford United. He joined the starting line-up for Leeds' 2–1 victory against Premiership side Everton on 25 September. He continued in the Cup run until a defeat by Manchester City. In November 2012, Portsmouth made a loan bid to sign Ashdown for the second time, but the bid was rejected.

In 2013, Ashdown set up an online business, Trusted Pro Supplements, supplying and offering information to athletes about nutritional supplements that do not feature on banned substance lists and are believed not to be harmful.

In the following season, Ashdown struggled with an injury but in March 2012 he was established as number one for the rest of the 2011–12 season as the only goalkeeper for Portsmouth. Later that season, Portsmouth were relegated to League One after losing to Derby County 2–1 on 21 April 2012. At the end of the season, Ashdown was released along with Ricardo Rocha and Benjani, the three being told that they would not be offered new contracts because of the club's ongoing financial problems. After being released, Ashdown said it was a difficult decision to leave Portsmouth and wished the club every success in the future. Ashdown then supported the bid for the fans to buy back their club, managing to convince 10 other players to pledge their £1000 and paying his towards the fans' successful bid to take over control of Portsmouth.

After a trial at Middlesbrough on 23 July 2012, Ashdown chose to join Leeds United along with Andy Gray following a trial at the club. Ashdown joined up with former Portsmouth teammates Jason Pearce, David Norris and Luke Varney and faced competition from newly signed goalkeeper Paddy Kenny for the first-choice goalkeeper position ahead of the new season. Ashdown was allocated the number 12 shirt for the 2012–13 season on 3 August.

After returning to Portsmouth, Ashdown got more game time as first choice, with 50 appearances including the League Cup and FA Cup in a season which Portsmouth finished 16th in the Championship. Ashdown's proudest moment in a Portsmouth shirt was when he broke a post-war club record for most minutes without conceding a goal (636 minutes) between February and March 2011.

Due to the intense competition for the goalkeeper's spot at Fratton Park, Ashdown was given the opportunity to go out on loan, Portsmouth deciding that this would help his career, and he joined Norwich City. He played the first game of a loan spell with Norwich City on 21 October 2006 in a 1–0 win against Cardiff City at Carrow Road, replacing Paul Gallacher in the starting XI.

Ashdown returned in late 2006 and but did not feature in the first team due to the presence of David James during the 2006–07 season. Ashdown picked up an FA Cup winners' medal with Portsmouth in 2008, but it was subsequently stolen. The stolen medal never resurfaced and the FA reissued Ashdown with a winners' medal. Despite not playing in the FA Cup win he made 3 appearances in the 2007–08 season. In the 2008–09 season Portsmouth played their first ever European match, against Vitória de Guimarães, which they won and thus qualified for the group stages of the UEFA Cup. After playing six league games during Portsmouth's 2009–10 Premier League relegation season, Ashdown was released by the club. However, before the start of the following season, he rejoined Portsmouth as their first-choice goalkeeper after David James' departure to Bristol City.

In August 2005, Portsmouth signed another goalkeeper, Sander Westerveld, and Ashdown was in competition with him at the beginning of the 2005–06 season for a first-team place. Westerveld started the season as first-choice 'keeper. However, after a number of poor performances by Westerveld he was dropped and Ashdown was again called on as Portsmouth's number one goalkeeper. With the return of former manager Harry Redknapp, Ashdown was dropped to second choice again after the arrival of Dean Kiely from Charlton Athletic in January 2006. In the 2006–07 season Ashdown faced even more competition from new high-profile signing David James.

Ashdown began his career at Reading, where he established a reputation as an exciting prospect. Following loan spells at Gravesend & Northfleet, Bournemouth and Rushden & Diamonds, and a work experience placement at Arsenal, Ashdown broke into Reading's first-team squad as a result of an injury to first-choice 'keeper Marcus Hahnemann. He made 13 appearances for the Royals but in the summer of 2004 Ashdown declined Reading's offer of a new contract and instead signed for Premier League club Portsmouth before the start of the 2004–05 season to provide competition for Shaka Hislop, with a view to replacing the veteran on his retirement.

Jamie Ashdown (born 30 November 1980) is an English retired footballer who spent a large part of his career as a goalkeeper for Portsmouth, for whom he made the majority of his professional appearances.