Jamieson spent the first five years of his career at Largs Thistle after leaving the Greenock Morton youth academy.[4] During his five years at the club Jamieson made over one hundred and fifty appearances for the Junior side.[3]
In June 2019 Jamieson completed a move to Scottish League Two side Queen's Park, in his only year with 'The Spiders' he made the league's Team of the Season.[4][5]
On 22 July 2020 Jamieson signed for Scottish Championship outfit Alloa Athletic ahead of the 2020–21 season.[5]
At the start of season 2021-22 Jamieson signed a loan deal from Alloa Athletic In January 2022, Jamieson signed a permanent contract until summer 2023. In February 2022, he picked up cinch League 2 Player of the Month. At the conclusion of season 2021-22, Jamieson was named as Stenhousemuir Player of the Year.
At the conclusion of season 2022-23, Jamieson was named as Stenhousemuir Player of the Year.
In January 2024, Jamieson extended his contract at Stenhousemuir until Summer 2026.
Following Stenhousemuir becoming cinch Scottish League 2 Champions, in April 2024, Jamieson was named in League 2 Team of The Year.
At the conclusion of season 2023-24, Jamieson was named as the supporters Player of the Year and was also named as the Player's Player of the Year.
Due to injury , in season 2024-25, Jamieson made only 3 Scottish League Cup appearances.
In season 2025-26, Jamieson returned to the team , but injury limited him to 6 appearances and he dropped out of the team before making his return in November 2025 v Dumbarton in the Scottish League Challenge Cup.
In April 2026, Jamieson extended his contract with Stenhousemuir for another year.
