Profile

The inaugural winner of Town sponsors’ Samsung’s “Win a Pro Contract” competition, Bradford-born striker Jackson had played youth football in Yorkshire including a spell at Bradford City which was ended by a back injury, but was working as a personal trainer and playing semi-pro before entering the competition after seeing a Facebook advertisement. Six months later, he was Paolo Di Canio’s selection to win the professional contract, but with the Italian leaving a few months later, Jackson never really got a chance with the Swindon first team.

At the time, few eyebrows were raised and the competition was seen as a bit of a publicity stunt. Later, Jackson looked like one that got away. Having been released by Town after his 12-month contract expired, having not made a matchday squad and spent time on loan at Oxford City and Swindon Supermarine, Jackson dropped into non-league with Tamworth and then Wrexham before a move to Barnsley. His career took off in 2017 when he joined Accrington, scoring 16 times in 45 games and earning a seven-figure transfer to Ipswich Town in 2018.

Career details

Club	Details
Guiseley Guiseley	2005 (schoolboy)
Bradford City Bradford	2011 (schoolboy); released
Field Sports and Social Field Sports & Social	(youth)
Blackburn Rovers Blackburn	(trial)
Leeds United Leeds United	(trial)
Albion Sports Albion Sports
Swindon Town Swindon	July 1st, 2013 (announced April 7th, 2013) ; released (rptd May 3rd, 2014)
Swindon Supermarine Supermarine	August 27th, 2013 (loan); recalled from loan (rptd October 29th, 2013)
Oxford City Oxford City	October 31st, 2013 (loan); expired (May 2014)
Tamworth Tamworth	rptd July 21st, 2014 (unattached); released (2014/5)
Wrexham Wrexham	July 1st, 2015 (announced June 26th, 2015) (unattached); transferred out (rptd May 23rd, 2016)
Barnsley Barnsley	rptd May 23rd, 2016 (transferred in, undisclosed fee); transferred out (July 21st, 2017)
Grimsby Town Grimsby Town	July 22nd, 2016 (loan); contract terminated (rptd February 4th, 2017)
Accrington Stanley Accrington	July 21st, 2017 (transferred in, undisclosed fee); transferred out (August 9th, 2018)
Ipswich Town Ipswich Town	August 9th, 2018 (transferred in , £1,000,000 ); released (rptd June 3rd, 2024)
Derby County Derby County	July 2nd, 2024 (unattached)