A 2-0 victory away to Queen's Park saw East Fife move to the top of the Scottish League Two table, only ahead of Elgin City due to alphabetical order as both sides now boast the same points tally and goal difference.
Kyle Macleod's 12th-minute strike was enough to see City through, despite a late rally from Stirling who saw an effort cleared off the line in the final minutes of the fixture.
Graham Webster gave Montrose a lifeline soon after the break, but Osadolor struck again in the 83rd minute to effectively seal the victory.
Ross McCord gave Montrose a late consolation goal from the penalty spot just before the final whistle was blown.
A late Darren Ramsey strike meant the sides shared a point each at Shielfield Park.
Higgins's second came instantly after Sheperd's strike to ensure victory for the home side.
Results in full (half-time scores in brackets): Annan Athletic 3-2 Montrose (2-0), Berwick Rangers 2-2 Arbroath (2-1), Clyde 3-1 East Stirlingshire (0-0), Elgin City 1-0 Stirling Albion (1-0), Queen's Park 0-2 East Fife (0-1).