Jackson started his career with his local team in Canada, Sunoco FC. He was invited to have trials with Gillingham, but was rejected by the club. At the age of 15, he moved to England and lived with his grandmother in Croydon, South London. While playing for Dulwich Hamlet, Jackson worked at McDonald's to sustain his move to England.
On January 4, 2009, Jackson scored an equalizing goal for Gillingham in their 2–1 FA Cup third round defeat by Aston Villa. He scored both goals as Gillingham beat Rochdale in the 2008–09 play-off semi final, and the 90th-minute winner in the 1–0 win against Shrewsbury Town in the final, as Gillingham returned to League One one year after relegation.
Jackson signed for Norwich in July 2010, signing a two-year contract with the club, with the option for another year, in a deal which saw striker Cody McDonald move to Gillingham on loan. He was given the number 10 jersey upon his arrival at the club and made his debut in a 3–2 home loss to Watford on August 6, 2010. He scored his first goal for the club against Swansea City on August 21. Manager Paul Lambert often used Jackson as an impact substitute due to the form and partnership of Grant Holt and Chris Martin. Jackson was given a start against Bristol City, and scored a brace, with a goal in each half at Ashton Gate. Jackson started the next four games again, in favour of Martin. He scored his fourth goal of the season in the 1–0 win over Middlesbrough on October 23. After a few months of mostly coming in as a substitute again, on April 2, 2011, Jackson scored his first hat-trick for Norwich, coming on as a substitute and scoring three times in the last twenty minutes of the match against Scunthorpe United at Carrow Road. He went on to score the goal that clinched Norwich's promotion to the Premier League, a late winner against Portsmouth.
Jackson made his Premier League debut on August 21, 2011, as a second-half substitute for Chris Martin in the second game of the season against Stoke City, the game finished with a Kenwyne Jones stoppage time header which resulted in a 1–1 home draw for Norwich.
Following his Premier League debut, Jackson began to struggle finding minutes in the team, he did not play a minute of football in the league until October 1 as a second half sub against Manchester United. Jackson made his first start in the Premier League on November 26 in a 2–1 victory over Queens Park Rangers, this was the first time a Canadian international had started in the Premier League since David Edgar on May 24, 2009, with Burnley. Jackson scored his first Premier League goal on December 20 against Wolverhampton Wanderers when he converted a Steve Morison cross one minute after being subbed on. Jackson came on as a second half sub against Fulham on December 31 and scored the game tying goal in second half injury time to earn a 1–1 home draw. In the fourth round of the FA Cup in late January Norwich was drawn against West Bromwich Albion, Jackson came off the bench in the 65th minute with the game being tied at 1–1 and scored the winning goal in the 85th to take the Canaries into the fifth round. After failing to make an appearance for almost a month Jackson returned to the starting line up in a 3–3 away draw on 5 May against Arsenal. The following week, Jackson was given the start again in the final game of the season against Aston Villa, the game ended in a 2–0 home victory with Jackson and Grant Holt as the scorers. Jackson finished the 2011–12 campaign for Norwich having made 22 appearances, starting in 10 of those. He scored three goals and registered two assists, with 34 shots on goal in his debut Premier League season. The club took up the option to extend Jackson's contract for another year in June 2012, along with David Fox and Elliott Ward. On August 25, 2012, he scored his first goal of the new season in a 1–1 draw at home to Queens Park Rangers. At the end of the season, Jackson was released by Norwich, having struggled to find minutes during his second year in the top flight.
On February 1, 2014, a day after his Eintracht Braunschweig contract was terminated, Jackson agreed to join Championship side Millwall on a deal until the end of the season. He made his debut against Brighton & Hove Albion on March 1, 2014. Jackson scored his first goal on March 25 in a 3–2 home defeat to Birmingham City.
After leaving Coventry at the end of the 2014–15 season, Jackson went on trial at fellow League One side Barnsley. On September 3, 2015, he signed a short-term contract to keep him at the club until January 3, 2016.
He was released by Walsall at the end of the 2017–18 season.
Jackson qualified for Canadian citizenship by virtue of his years of residence there as a child, and currently[when?] has 45 caps for Canada, scoring six times. He also has seven caps for the Canadian men's youth (under-20) team. His first game was a friendly against Brazil in May 2006, and he played in all three of Canada's games at the 2007 U-20 World Cup, his last games at that level. On November 14, 2008, he received his first call up for the Canadian senior squad for a match against his country of birth, Jamaica.
In the summer of 2013, Jackson was selected for his third consecutive Gold Cup, but after playing in the first group stage game against Martinique he left with the team's blessing to join his new German club and was replaced by Kyle Porter for the remainder of the tournament.
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"Blackburn 1–2 Leeds". BBC Sport. March 12, 2016. Retrieved March 12, 2016. https://www.bbc.co.uk/sport/football/35732984
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Simeon Jackson – FIFA competition record (archived) https://web.archive.org/web/20150905/http://www.fifa.com/fifa-tournaments/players-coaches/people=268611/index.html
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Simeon Jackson at Soccerbase https://www.soccerbase.com/players/player.sd?player_id=39168
"A-Z of Diamonds: Simeon Jackson". Rushden & Diamonds FC. July 16, 2010. Archived from the original on April 7, 2012. Retrieved April 27, 2011. https://web.archive.org/web/20120407124819/http://www.thediamondsfc.com/page/A-ZofDiamonds/0%2C%2C10784~1253954%2C00.html
Appearance(s) in Northamptonshire Cup /wiki/Northamptonshire_Cup
"A-Z of Diamonds: Simeon Jackson". Rushden & Diamonds FC. July 16, 2010. Archived from the original on April 7, 2012. Retrieved April 27, 2011. https://web.archive.org/web/20120407124819/http://www.thediamondsfc.com/page/A-ZofDiamonds/0%2C%2C10784~1253954%2C00.html
Appearance(s) in Northamptonshire Cup /wiki/Northamptonshire_Cup
"A-Z of Diamonds: Simeon Jackson". Rushden & Diamonds FC. July 16, 2010. Archived from the original on April 7, 2012. Retrieved April 27, 2011. https://web.archive.org/web/20120407124819/http://www.thediamondsfc.com/page/A-ZofDiamonds/0%2C%2C10784~1253954%2C00.html
Appearance(s) in FA Trophy /wiki/FA_Trophy
"A-Z of Diamonds: Simeon Jackson". Rushden & Diamonds FC. July 16, 2010. Archived from the original on April 7, 2012. Retrieved April 27, 2011. https://web.archive.org/web/20120407124819/http://www.thediamondsfc.com/page/A-ZofDiamonds/0%2C%2C10784~1253954%2C00.html
Two appearances in FA Trophy; one appearance in Northamptonshire Cup
"Games played by Simeon Jackson in 2007/2008". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=137
"Games played by Simeon Jackson in 2008/2009". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=138
Three appearances three goals in League Two play-offs; one appearance in Football League Trophy /wiki/EFL_League_Two_play-offs
"Games played by Simeon Jackson in 2009/2010". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=139
Appearance(s) in Football League Trophy
"The English National Football Archive". enfa.co.uk. Retrieved July 8, 2022. https://www.enfa.co.uk/
Soccerbase's stats for the match between Doncaster Rovers and Norwich City on 14 September 2010 fail to include Jackson's substitute appearance for Norwich.[68][69] Therefore, until and unless they correct it, he should have one more appearance for Norwich than given on his Soccerbase page.
"Games played by Simeon Jackson in 2011/2012". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=141
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"S, Jackson". Soccerway. Perform Group. Retrieved March 8, 2018. https://us.soccerway.com/players/simeon-jackson/50554/
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"Games played by Simeon Jackson in 2014/2015". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=144
Appearance(s) in Football League Trophy
"Games played by Simeon Jackson in 2015/2016". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=145
Appearance(s) in Football League Trophy
"Games played by Simeon Jackson in 2015/2016". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=145
"Games played by Simeon Jackson in 2016/2017". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=149
Appearance(s) in Football League Trophy
"S, Jackson". Soccerway. Perform Group. Retrieved March 8, 2018. https://us.soccerway.com/players/simeon-jackson/50554/
Soccerbase also have Jackson making a substitute appearance in the Football League Trophy against Shrewsbury Town on 7 November 2017.[77] However, Soccerbase have four substitutes appearing for Walsall in this game, which was against regulations at the time. Other sources have Jackson as an unused substitute.[67][78][79]
"Games played by Simeon Jackson in 2017/2018". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=150
"Games played by Simeon Jackson in 2018/2019". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=151
"Games played by Simeon Jackson in 2019/2020". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=152
"Games played by Simeon Jackson in 2019/2020". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=152
Appearance(s) in Football League Trophy
"S, Jackson". Soccerway. Perform Group. Retrieved March 8, 2018. https://us.soccerway.com/players/simeon-jackson/50554/
"S, Jackson". Soccerway. Perform Group. Retrieved March 8, 2018. https://us.soccerway.com/players/simeon-jackson/50554/
Appearance(s) in FA Trophy /wiki/FA_Trophy
"Games played by Simeon Jackson in 2020/2021". Soccerbase. Centurycomm. Retrieved March 9, 2021. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=153
"Simeon Jackson (CAN)". Canada Soccer. Retrieved March 8, 2018. https://www.canadasoccer.com/index.php?pid=1590&t=profile&
"S, Jackson". Soccerway. Perform Group. Retrieved March 8, 2018. https://us.soccerway.com/players/simeon-jackson/50554/
"Games played by Simeon Jackson in 2008/2009". Soccerbase. Centurycomm. Retrieved January 21, 2020. https://www.soccerbase.com/players/player.sd?player_id=39168&season_id=138
"Jackson is male selection for 2009 Canadian Players of the Year award". Canada Soccer. December 18, 2009. Archived from the original on June 5, 2011. https://web.archive.org/web/20110605070612/http://www.canadasoccer.com/news/viewArtical.asp?Press_ID=3913
"Jackson among Canada's players of the month". toronto.citynews.ca. February 10, 2012. Retrieved March 13, 2022. https://toronto.citynews.ca/2012/02/10/jackson-among-canadas-players-of-the-month/
"Norwich City's Simeon Jackson named Championship Player of the Month". Eastern Daily Press. May 6, 2011. Retrieved March 13, 2022. https://www.edp24.co.uk/sport/norwich-city/norwich-city-s-simeon-jackson-named-championship-player-of-the-474944