Career
Early career
Jackman started his career at Premier League side Aston Villa as a trainee. However, Jackman never played for the first team although he did spend two loan spells. The first at Cambridge United, the second at Stockport County.
Young Jackman had clearly made an impression at Stockport as they snapped him up in the middle of his loan spell for a fee of £70,000 in the 2003/04 season.
Over the next season and a half, Jackman made 54 league appearances (9 as a substitute) scoring 5 goals. Gillingham
At the beginning of the 2005/06 season Jackman joined recently relegated League One side Gillingham.
After a difficult start, during which the entire team struggled for results, Jackman found himself playing in the left wing position as well as the left back position. He was awarded the "goal of the season" for 2006-2007 for a goal at home to Brentford.
Northampton Town
He was offered a new contract with the Kent club but instead opted to sign for Northampton Town on 23 May 2007.
After a fine first season with the club Jackman was voted the player of the year for the 2007-2008 season. He signed a one-year contract extension with the club on 24 July 2008. Jackman has scored several goals in the 2008-2009 season after being handed free-kick duties by Northampton manager Stuart Gray.
Return to Gillingham
Jackman rejoined Gillingham on 25 August 2009, making his first appearance as a substitute in a Football League Cup game against Blackburn Rovers the same day.
Jackman went on to make 24 appearances on his return season, however he missed out nearly four months of football during the season with a dislocated shoulder. Foreign the 2010-2011 season, again Jackman suffered with injuries with this time suffering from a recurring knee injury.
This limited his amount of game time to just 17 appearances in which he scored one goal. He was Gillingham"s player of the season 2011/12.
Kidderminster Harriers
On 28 January 2013, Jackman was said to be frustrated with the lack of first team action at Priestfield and opted to sign for play-off hopefuls Kidderminster Harriers, currently in the Conference Premier.
Jackman rejected two League clubs to sign for a club situated in his home county. Worcester City
On 20 July 2014, Jackman signed a contract with Worcester City.