[14] He made his league debut as a substitute for Chris Barker in Cardiff's Championship defeat at home to Norwich City on 22 April 2006.

[15] In November 2006 the Torquay-based newspaper the Herald Express reported that Jacobson was likely to sign for Torquay United on loan, a story backed up by the team's official website.

[5] Jacobson was the subject of controversy after executing a tackle on Kieron Dyer during a second round League Cup match against West Ham United on 28 August 2007.

[20] During his spell at Rovers, he was voted Young Player of the Year and helped the team to promotion to League 1 and to the quarter final of the FA Cup, scoring in a penalty shoot out win against Premiership Fulham.

[30] In the 2011–12 season he made 45 appearances for Shrewsbury Town in all competitions establishing himself as first-choice left-back with manager Graham Turner and securing promotion to League One.

[31][32] In the 2012–13 season, he was selected as captain in the absence of Matt Richards as Shrewsbury confirmed their League One status in a 0–0 draw away at Colchester United on 20 April 2013.

[34][35] By playing an undisclosed number of matches for Shrewsbury Town, Jacobson triggered a clause in his contract to earn another year, extending his stay to the end of the 2013–14 season.

[38] In the 2015 League Two play-off final, Jacobson's free kick was deflected into his own net by Southend United's goalkeeper Daniel Bentley to open the scoring.

[42] In the 2020 League One play-off final, Jacobson scored the winning goal from the penalty spot as the club reached the Championship for the first time.

[50] Jacobson captained the Wales Under-21 side that beat France and Romania until narrowly losing over two legs to England U21 in the 2009 European Championship play-offs in October 2008.