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On 11 June 2019, it was announced that Bowery would join newly-promoted League One club Milton Keynes Dons on a free transfer effective from 1 July 2019. He scored his first goal for the club in a 3–2 defeat away to Wycombe Wanderers.

He moved to Crewe Alexandra on loan in January 2017, and scored his first Crewe goal on 14 March at Crawley Town. On 9 May 2017, Crewe announced that Bowery would be returning to his parent club, however two weeks later on 23 May, Crewe announced that Bowery had signed a two-year contract with the club, as his Leyton Orient contract included a relegation release clause which allowed him to leave. After scoring 22 times in 99 games over two seasons, he was offered a new contract by Crewe at the end of the 2018–19 season, but declined to extend his stay at Gresty Road.

On 5 July 2016, Bowery joined Leyton Orient on a two-year deal upon his release from Oxford United.

On 10 June 2014, Bowery joined Rotherham United for an undisclosed fee, breaking the Millers' transfer record of £160,000 for Lee Frecklington in January 2013. He signed on loan for Bradford City in November 2015. He left Rotherham by mutual consent in January 2016.

After beginning his career with Derby County, Bowery had an extended spell at Chesterfield, coming through their youth team to make over 100 appearances in all competitions for them. While with Chesterfield he also had a short loan spell with Barrow. Bowery moved to Aston Villa in 2012; in 2014 he had a short loan spell with Doncaster Rovers. He moved to Rotherham United in 2014; in 2015 he had a short loan spell with Bradford City. He then moved to Oxford United and then Leyton Orient, and in 2016 went on loan to Crewe Alexandra; after Orient's relegation, Bowery exercised a relegation release clause which allowed him to leave and sign for Crewe. After two seasons with Crewe, he rejected a new contract offer to sign for Milton Keynes Dons.

Bowery signed for Aston Villa on 31 August 2012. He signed on loan for Doncaster Rovers in February 2014.

Born in Nottingham, Bowery represented Derby County as a schoolboy but was not signed as a scholar and eventually moved on to Chesterfield. Bowery made his professional debut for Chesterfield on 30 August 2008, in a 1–0 defeat against Wycombe Wanderers. On 19 November 2009, Bowery joined Conference National club Barrow on loan for six weeks. Bowery scored his first goal in the Football League on 29 January 2011, in a 2–2 home draw against Bradford City. On 15 September 2011, Bowery signed a contract extension to keep him at the club until June 2014.

Jordan Nathaniel Bowery (born 2 July 1991) is an English professional footballer who plays as a forward for League One club Milton Keynes Dons.