It was a weekend for all Angus sides to forget, with all four teams failing to securing a single point.
In League One, Arbroath welcomed League One Champions Rangers to Gayfield.
They always had a tough task on their hands to get a win from their home match against Rangers, but the Lichties came agonisingly close to earning a draw.
Rangers took the lead in the 19th minute, thanks to Jon Daly, but Arbroath pulled themselves level in the 61st minute, with Paul McManus netting the vital goal.
As the match drew to a close it looked likely that Arbroath would earn a much needed point as they look to stave off relegation, but Fraser Aird broke Lichties’ hearts when he fired home a late winner in the 87th minute.
Brechin City travelled to take on second placed Dunfermline and another late goal proved costly.
Dunfermline took the lead in the 48th minute through Lawrence Shankland, before Robert Thomson equalised in the 60th minute.
However, a last minute penalty, taken by Ross Millen, handed the Pars all three points - leaving City just one point above the relegation play-offs.
Forfar Athletic suffered a 2-1 defeat at home to East Fife, who are battling to avoid the relegation play-offs.
Forfar took the lead through Chris Duggan in the 32nd minute, but just three minutes later Liam Buchanan equalised for the Fifers.
Nathan Austin wrapped up the three points at the end of the first half.
This Saturday, Brechin are hosting Ayr United, while Arbroath travel to face Stenhousemuir. Forfar Athletic have the weekend off.
In League Two, Montrose suffered a three nil defeat at home to Elgin City. Elgin took the lead in 53rd minute through Shane Sutherland, before Adam MacLeod scored twice in the 75th and 86th minutes to ensure the victory.
Montrose travel to face top of the table Peterhead this weekend.