Striker Simeon Jackson signed for Norwich City from Gillingham on 16th July 2010 for a fee reported to be £600,000 and a year's loan for Cody MacDonald at Priestfield.The 23-year-old Canadian international put pen to paper on a two-year deal. Norwich also have a further one-year option on keeping the striker beyond his first two seasons at Carrow Road.

“I'm delighted to have Simeon at the football club, he'll be a great addition to the squad and will put pressure on the other lads,” said manager Paul Lambert. “He's a goalscorer, scored loads of goals for Gillingham the last two seasons and is an international striker. We first saw him at Rushden and Diamonds, where his goalscoring record was brilliant and obviously came up against him last season when he was at Gillingham.”

Jackson was born in Kingston, Jamaica but grew up in Mississauga, Ontario. He played for 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.

He joined Rushden & Diamonds in 2004 and was the club's top scorer in the 2006–07 season, scoring 20 goals. The next season he was top scorer for the Diamonds in the league, scoring 16 goals, During his time with the Diamonds, he had In 2005, trials with Manchester United and Manchester City. When he left the Diamonds he had established himself as the club's 8th highest goalscorer, scoring 43 goals in just over 100 games in all competitions.

In January 2008, he signed with Gillingham, for a transfer fee of £150,000 on a three-and-a-half-year contract. He made his debut against Cheltenham Town on 2nd February 2008.

Jackson qualified for Canadian citizenship by virtue of his years of residence there as a child. He has seven caps for the Canadian Men's Youth (U-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 FIFA U-20 World Cup, his last games at that level. On 30th May 2009, Jackson made his debut for for Canada against Cyprus, scoring the winning goal in the 53rd minute of a 1–0 victory. On 18th December 2009, Jackson was named the 2009 Canadian Player of the Year.

Simeon made his City debut in the 3-2 home defeat to Watford on 6th August 2010. He scored his first goal for Norwich in the 2-0 win over Swansea on 21st August 2010 and his first hat-trick in the 6-0 drubbing of Scunthorpe on 2nd April 2011. His second hat-trick came on 25th April 2011 in the 3-2 win over Derby. Jackson then scored the winner in the 1-0 victory over Portsmouth on 2nd May 2011 that secured Norwich's promotion to the Premier League. He finished the season with 41 appearances and 13 goals

The following season Simeon made 26 appearances and scored five goals as Norwich finished 12th in the Premier League

The following season saw Simeon make 19 appearances, scoring three goals. On 20th May 2013, Norwich announced that they would renew Jackson's contract when it expired at the end of June 2013. He had made a total of 86 appearances for Norwich, scoring 21 goals.

Despite reports linking Jackson with Bournemouth and Millwall, he signed for newly promoted Bundesliga side Eintracht Braunschweig on a two year deal on 10th July 2013.

On 21st January 2014, Simeon was linked in the media with a return to England to join Charlton. He was released by Eintracht Braunschweig on 31st January 2014 and signed for Millwall the following day.

Jackson scored two goals in 14 appearances for Millwall but was released at the end of the 2013/14 season.

On 18th August 2014, he signed a one year contract with Coventry City. "Simeon is a player that has played and scored at the highest level. He's got a great attitude and he knows what promotion requires. His experience will be a huge benefit to the younger players in the dressing room. His goal-scoring record throughout the leagues also speaks for itself and I'm looking forward to his arrival taking the competition for places among the strikers up another gear." said boss Steven Pressley

Jackson was one of eight Sky Blues released by the club on 19th May 2015. He had scored three goals in 30 appearances.

He joined MLS side Chicago Fire on trial in June 2015 but returned to the UK to trial with Barnsley the following month. He was later linked with Southend before signing for Barnsley on a short term contract on 2nd September 2015 until January 3rd 2016. Barnsley boss Lee Johnson said: "He's somebody who's got that experience of promotions and scoring goals at this level."

He made 11 appearances for Barnsley but was released at the beginning of January 2016. he joined Paul Lambert's Blackburn on trial before signing a short term contract on 15th January 2016 until the end of the 2015/16 season.

On 21st May 2016, it was announced that Jackson and seven other players were free to leave the club at the end of their contract in June 2016, although of course any new manager might choose to re-sign them. he had scored twice in 19 appearances.

Jackson signed a two year contract with League One side Walsall on 18th July 2016. He will help plug the gap left by Tom Bradshaw, who has moved to Oakwell in the pursuit of Championship football.  Jackson said "I want to come here, play as many games as I can, score goals and cause defenders problems. It's a new challenge for me being a senior in the changing room, but from what I know and have seen in my short time here, the set-up looks really good. The club just missed out [on promotion] last season and hopefully they can learn from it and be up there again this year."

On Transfer Deadline Day (31st January 2018), Jackson joined Grimsby on loan until the end of the 2017/18 season. He had played 51 games for Walsall but only 10 of these were in 2017/18. He made his debut against Cheltenham on 3rd February 2018. Grimsby teammates with a Norwich connection include Ben Killip, Reece Hall-Johnson, Sam Kelly and Diallang Jaiyesimi.

He was released by Walsall on 11th May 2018.

On 28th September 2018, he joined St Mirren until January 2019 with an option to extend until the end of the season.Speaking on the move, Simeon said: "I'm delighted to be here and can't wait to get going. The lads have welcomed me in really well. It's happened really quick but it's been good. The manager was a great guy to meet and as soon as I met him I got a good feeling and I'm looking forward to working with him."

St Mirren manager, Oran Kearney said: "He fits the bill for what we are needing at this point in time He's been about the Championship in England for a long time and his pedigree goes before him. When he arrives in and you see the shape he's kept himself in it's obvious he is a top professional. He'll be well liked around the place and he'll be a good influence on everybody around the club." 

He left St Mirren when his contract expired in June 2019 but signed for Kilmarnock in October 2019 until January 2020. On 30th December 2019, the Killies announced that they would not be extending Simeon's contract. He had played four games for the Kilmarnock first-team.

On 20th January 2020 Jackson returned to English football signing for Stevenage until the end of the 2019/s0 season. After only five appearances in all competitions Jackson was released by the club at the conclusion of the 2019–20 season, which saw the Hertfordshire club relegated.

After spending some time with Chelmsford City, on 8th March 2021 he joined Kings Lynn on loan until the end of the 2020/21 season as Chelmsford's National League South campaign was cancelled due to Covid-19. Jackson knows Lynn boss Ian Culverhouse from when Culverhouse was his Assistant Manager at Norwich. After six goals in 17 appearances for the Linnets, he returned to Chelmsford on 3rd July 2021 combining his playing with the role of Head of Coaching and as Community Ambassador. Speaking on his return to the Club, Simeon said: "It feels great, I'm glad to get it tied up and I'm looking forward to the season now. After speaking to the Chairman and [Robbie], they put together something that was really appealing. Obviously, I'm towards that side of the game where you have to look at other things and the coaching side is something that I'm interested in; I'm glad that I can help here and play a part of that."

He announced his retirement from playing on 10th July 2023. He had scored 20 goals in 68 appearances for Chelmsford.

Jackson came out of retirement on 3rd April 2024 to sign for AFC Sudbury of the Southern League Premier Division to help them avoid relegation although they were seven points from safety with four games remaining. He will combine this with coaching Chelmsford's Under-18s.