He started his career with Douglas Lads, then moving to Lincraig Boys Club from where he joined Dundee, and had loan spells at Montrose in 2011 and Alloa Athletic in the 2014–15 season.
Dundee-born Benedictus made his début for Dundee on 1 November 2008 against Airdrie United at Dens Park, playing the full match.
[8] During his lengthy 7-year stint in Kirkcaldy, Benedictus would quickly be named the club captain in his first season,[9] experience a shock relegation to the Scottish League One in 2017,[10] see a return to the Championship after winning the League One title in 2020,[11] lead a strong push to the Premiership play-offs the following season,[12] and winning two Scottish Challenge Cup titles.
[13][14] On 6 June 2022, Benedictus would sign a two-year deal with Raith's Fife rivals and Scottish League One side Dunfermline Athletic.
[16] On 15 April 2023, after an exemplary season as club captain, Benedictus led Dunfermline to the Scottish League One title which was confirmed after a 5-0 rout of Queen of the South.