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He scored his first goal of the 2019–20 season on 20 August, netting a 94th-minute winner in a 2–1 win over AFC Wimbledon at Portman Road. He scored 4 goals during August, including a brace in a 0–5 away win over Bolton Wanderers at the University of Bolton Stadium. His form earned him a nomination for the League One Player of the Month award.

Ahead of the 2018–19 season, Jackson was offered a new contract by the club, whilst attracting interest from other clubs following an impressive 2017–18 season. Jackson made one appearance in the 2018–19 season, in a 2–0 loss to Gillingham in the opening game of the season.

Jackson signed for Ipswich Town on 9 August 2018 on a three-year deal (with an option of a further 12 months) for an undisclosed fee. The move reported to cost £1 million, which was described by the Lancashire Telegraph as "Accrington Stanley's first million pound sale", and saw him reunited with manager Paul Hurst, having previously played under him at Grimsby Town. Ipswich Town managed to beat off competitions from "a number of Sky Bet Championship clubs" to sign him.

He made his Ipswich Town debut on 11 August, coming on as a substitute for Ellis Harrison, in a 1–0 loss against Rotherham United two days after signing for the club. Three days later, on 14 August 2018, Jackson scored his first goal for the club against Exeter City in the first round of the EFL Cup, with Ipswich eventually losing 4–2 in a penalty shootout after the game finished 1–1. He made 38 appearances in all competitions over the course of the 2018–19 season, scoring 4 goals.

Jackson returned to his parent club Barnsley in February 2017 after his season long loan was retracted. Despite suffering an injury and eventually his place in the team following the departure of Paul Hurst, he went on to make twenty–four appearances in all competitions, scoring twice.

After impressing manager John Colemen while on trial, Jackson signed for Accrington Stanley for an undisclosed fee on a two-year contract on 21 July 2017.

Jackson scored on his debut for Accrington Stanley, on the opening game of the 2017–18 season, in a 3–1 win over Colchester United. For his performance throughout August, he was nominated for Sky Bet League Two's Player of the Month for August but lost out to Frank Nouble. Soon after joining the club, Jackson established himself in the starting eleven and formed an effective partnership with Billy Kee. Together, they helped contribute to the team's impressive form. In late September, he suffered a hip injury that saw him miss two matches. In a follow up match, he provided a hat–trick for the side, in a 4–0 win over Chesterfield. At the end of the 2017–18 season, Jackson had scored 16 goals in 44 league appearances, to help Accrington claim the EFL League Two title and earn promotion to EFL League One.

Jackson made his Wrexham debut as a substitute, in a 3–1 loss against Bromley in the opening game of the 2015–16 season. He spent the early part of the season appearing as a substitute. As the season progressed, Jackson earned his place in the starting eleven. On 23 February 2016 he scored his first goals for the club, netting a brace in a 2–0 win over Kidderminster Harriers. He was later praised by manager Gary Mills. At the end of the 2015–16 season, Jackson had made thirty–six appearances in all competitions, scoring four goals. Following an impressing debut season at the Racecourse Ground, Jackson was offered a new contract by Wrexham, with Jackson, himself, stating that he was keen to stay at the club.

After rejecting a new contract at Wrexham, he signed for Barnsley on 23 May 2016, signing a two–year contract with the club for an undisclosed fee.

He signed on loan for Grimsby Town in July 2016. He scored on his debut for the club in a 2–0 win over Morecambe on 6 August 2016. It wasn't until on 9 November 2016 when Jackson scored again, in a 4–2 loss against Sheffield United in the EFL Trophy. Throughout his time at Grimsby Town, Jackson found himself, competing for a place in the starting eleven.

Jackson was selected and called up to the England C team in March 2016, to play against Ukraine U23s. Jackson scored the second goal on his international debut in Kiev later that month, as England C ran out 2–0 winners.

On 26 June 2015, Jackson left Tamworth in favour of joining Wrexham on a one–year contract.

After leaving Swindon Town at the end of the 2013–14 season, he joined Tamworth on 21 July 2014.

In January 2013, Jackson was among eleven players taking part in the final of Samsung's Win A Pro Contract competition. He made it into the final cut, along with two other players. In March 2013, Jackson trained with the Swindon development team in a bid to win the 'Win a Pro Contract' competition and played a development team match. The following month, he signed for Swindon Town after winning the 'Win a Pro Contract' competition, signing a twelve-month contract on 1 July 2013.

During his loan spells away from Swindon Town, Jackson was monitored by his parent club in the hopes of making a breakthrough into the first team, with Manager Mark Cooper and local newspaper Swindon Advertiser spoke about. At the end of the 2013–14 season, however, the club released him, along with nine other players, after they decided against offering them a contract when it expired in the summer. Upon leaving the club, Jackson stated that he felt he had not been given a chance to establish himself at Swindon Town.

Jackson joined Swindon Supermarine on a month long loan in August 2013. The deal was extended for a further month in September 2013 after he had scored five goals in seven games for the club. In October 2013 his loan deal was again extended by a further month, although he was recalled from his loan spell by his parent club in late October.

After being recalled from his loan spell at Swindon Supermarine, he spent another loan spell at Oxford City, having joined them on 1 November 2013. The following day, Jackson scored on his Oxford City debut, coming on as a substitute, in a 3–2 win over Harrogate Town. On 20 December 2013, the loan was extended for the "next couple of months". On 31 January 2014, Jackson extended his loan spell until the end of the season. At the end of the 2013–14 season, Jackson had helped the side avoid relegation, as he made twenty–three appearances, scoring eight times.

Jackson made his Tamworth debut on 9 August, starting in a 0–0 draw against Harrogate Town in the opening game of the season. He scored his first goal for the club, in a 2–1 victory over Gloucester City. Jackson finished the season as a joint–top scorer, along with three other players, scoring 8 goals in 36 appearances for Tamworth.

Kayden Pastel Dunn Jackson (born 22 February 1994) is an English professional footballer who plays as a striker for Ipswich Town. He has also represented England C at international level.