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Fletcher claimed the number 11 shirt ahead of the 2019–20 season, the first season under new manager Jonathan Woodgate. He scored on the first day of the new season: a 3–3 draw at Luton Town on 2 August. Fletcher managed to push Britt Assombalonga out of the first-team. In January 2020, Fletcher won the Championship Goal of the Month award for December in recognition for his 30-yard volley against West Bromwich Albion, which ended in a 2–0 victory in Middlesbrough's favour.

On 31 January 2018, Fletcher made a deadline day switch to Sunderland, signing on loan for the remainder of the season. He scored his first goal for Sunderland in a 4–1 win at Derby County on 30 March 2018. Fletcher was a member of the Sunderland team that suffered relegation to League One at the end of the season, meaning that the club had suffered two consecutive relegations. Furthermore, his tenure at the club resulted in him appearing in the Netflix documentary series Sunderland 'Til I Die, released on 14 December 2018.

On 28 July 2017, Fletcher signed for Middlesbrough for a fee of £6.5 million, signing a four-year contract. He made his debut on 5 August 2017 against Wolverhampton Wanderers in a 1–0 defeat. His first goal for the club came as the last of three in a 3–0 win against Scunthorpe United on 22 August 2017 in the EFL Cup, his first in the league came in a 3–2 win over Queens Park Rangers on 16 September.

Fletcher signed for Barnsley on loan in January 2016. He scored on his professional debut on 9 January 2016, in a 1–1 draw with Fleetwood Town in the Football League Trophy Northern Area Final first leg, and scored his first league goal on 20 February 2016.

On 3 April 2016 he scored a goal in the 2016 Football League Trophy Final as Barnsley won the competition. On 29 May 2016, he scored the opening goal in Barnsley's 3–1 victory in the 2016 Football League One play-off Final against Millwall, helping Barnsley return to the Championship. In total Fletcher scored nine goals in 27 games for Barnsley during his spell at the club.

After impressing while on loan at Barnsley, Fletcher was offered a new contract at Manchester United amid interest from Championship side Leeds United. On 23 June 2016, it was reported that he had turned down the contract offer to stay at Manchester United but would continue to train at the club.

In July 2016, Fletcher signed a four-year deal with West Ham United.

He made his unofficial debut for West Ham United's Development squad on 15 July 2016 in a 2–0 pre-season friendly defeat away to Chelmsford City.

On 30 November 2016, Fletcher scored his first goal for West Ham, in a 4–1 defeat to Manchester United, in the EFL Cup quarter-final at Old Trafford.

In November 2015, Fletcher made his debut for the England under-20 side, scoring only 10 minutes after coming on as a substitute. In March 2016, he was called up to face the Canada under-20s, playing up front with his then Manchester United teammate Marcus Rashford, and scored in a 4–1 win.

Fletcher joined Bolton Wanderers at the age of nine, before moving to Manchester United at the age of 13. He signed his first professional contract with Manchester United in May 2014.

His West Ham debut came on 18 August in the UEFA Europa League when he was introduced as a last minute substitute for Andy Carroll in a 3–0 win over NK Domžale. His Premier League debut came again from the substitutes bench on 21 August when he replaced Håvard Nordtveit after 80 minutes, in a 1–0 win over Bournemouth.

Ashley Michael Fletcher (born 2 October 1995) is an English professional footballer who plays as a striker for Middlesbrough.