The draw for the first round of the Petrofac Training Cup - the newly-sponsored Challenge Cup - was made last week with a mixed draw for the Angus clubs.
Brechin City were given a difficult fixture away to Championship side Cowdenbeath, who will be no small threat despite the loss of star striker Kane Hemmings.
It’s Championship opposition for Arbroath as well as they are set to host Barry Smith’s Alloa Athletic side, who were recently buoyed by the re-signing of striker Greig Spence, who left Recreation Park for Celtic in 2009 for a club record six-figure sum.
Forfar Athletic have been drawn against East Fife once again, the second successive year the two sides will face each other at this stage of the Challenge Cup.
Montrose will face a side they know all about in Jim McInally’s Peterhead - newly promoted after winning Scottish League Two last year.
All ties are scheduled to take place on Saturday, July 26.
The Angus outfits could all be set for live slots on BBC Alba after the Scottish Professional Football League agreed a new broadcast deal that will see the Gaelic-language channel showing live coverage of 16 matches from across the Championship, League One and League Two.
Loons manager Dick Campbell has confirmed the signing of striker Dale Hilson on a one-year contract.
The 21-year-old striker featured for Forfar more than 100 times over four loan spells before his release from parent club Dundee United last month, and Campbell was swift to ensure the popular forward was offered a deal with the Station Park outfit.
Forfar started pre-season with a closed doors friendly against Preston Athletic, running out 7-0 winners.
Brechin continued their pre-season run with a 1-0 victory over Montrose, Ryan Ferguson netting the only goal of the game shortly before half time.
Arbroath will be hoping for a better result than their 7-0 loss to Aberdeen when they host Highland League side Brora Rangers at Gayfield Park on Saturday.
Montrose meanwhile have replaced their home game with Peterhead on July 15 with a tie against Dundee with a 7.15 p.m. kick off.