An England U-20 international, Jackson joined Swindon on loan from Tottenham Hotspur, in September 2002, shortly after another loanee, the popular Jimmy Davis, succumbed to an ankle injury. Jackson joined the Town when they were on the crest of a slump - his first match being a 2-0 defeat at Q.P.R., his second being another defeat by the same scoreline at Cheltenham - a match that involved some ugly scenes of arguments between fans and players. After six successive league defeats, Jackson helped the Town to a win in their next game, when he scored a free-kick in a 2-0 home win over Northampton.
Without ever being spectacular, Jackson featured in a total of 17 games over his loan period, scoring twice, the other goal coming in a 6-1 demolition of Southend in the LDV Vans Trophy - a result that ultimately saved Andy King's job. After returning to White Hart Lane, Jackson featured in the Tottenham first team for a period, but after several changes of management, found himself out on further loan periods with Championship clubs.
| Season | LEAGUE | FA CUP | EFL CUP | OTHER | TOTAL | |||||
|---|---|---|---|---|---|---|---|---|---|---|
| Apps | Gls | Apps | Gls | Apps | Gls | Apps | Gls | Apps | Gls | |
| 2002/03 | 12 (+1) | 1 | 2 | - | - | - | 2 | 1 | 16 (+1) | 2 |
| TOTAL | 12 (+1) | 1 | 2 | - | - | - | 2 | 1 | 16 (+1) | 2 |
| Club | Details |
|---|---|
Tottenham Hotspur
Tottenham |
1999 (youth)
March 23rd, 2000 ; released (rptd June 20th, 2006) |
Swindon Town
Swindon |
September 13th, 2002 (loan); expired (December 13th, 2002) |
Colchester United
Colchester United |
March 11th, 2003 (loan); expired (2004/5) |
Coventry City
Coventry City |
November 21st, 2003 (loan); recalled from loan (rptd December 24th, 2003) |
Watford
Watford |
December 23rd, 2004 (loan); expired (rptd March 21st, 2005) |
Derby County
Derby County |
September 16th, 2005 (loan); contract terminated (rptd November 15th, 2005) |
Colchester United
Colchester United |
July 31st, 2006 (announced June 20th, 2006) (unattached); transferred out (August 17th, 2009) |
Notts County
Notts County |
August 17th, 2009 (transferred in, undisclosed fee); transferred out (July 8th, 2010) |
Charlton Athletic
Charlton Athletic |
February 18th, 2010 (loan); contract terminated (March 11th, 2010) |
Charlton Athletic
Charlton Athletic |
July 8th, 2010 (transferred in, free transfer)
rptd April 30th, 2017 (appointed player-coach); retired (rptd May 18th, 2018) rptd March 22nd, 2018 (appointed assistant manager) rptd May 18th, 2018 (appointed coach) March 15th, 2021 (appointed caretaker manager) October 21st, 2021 (appointed caretaker manager) December 17th, 2021 (appointed manager); sacked (May 3rd, 2022) |
AFC Wimbledon
Wimbledon |
May 16th, 2022 (appointed manager) |