Highland League sides Formartine United, Fraserburgh and Brora Rangers led the way last season as the only first round entrants to make it as far as round three, with Brora famously knocking out Hearts after a 2-1 win in round two.
Lowland League outfit Bonnyrigg Rose also came agonisingly close to knocking out Premiership-bound Dundee on their own patch in the second round, twice taking the lead through Lee Currie penalties only to bow out 3-2 after extra-time.
The Midlothian outfit start their latest adventure with a trip to Mosset Park to face Highland League side Forres Mechanics.
Brora travel to Meggetland in Edinburgh to face a Tynecastle side still without a manager following the recent departure of Stevie McLeish to Penicuik, who host fellow East of Scotland Premier Division leaders Tranent in a 2.30 pm kick-off.
Highland League leaders Fraserburgh, who gave Montrose a tough afternoon in last season's third round before falling to a 4-2 defeat, get their tournament up and running at home to Sauchie Juniors.
Elsewhere, Spartans are up against familiar opponents as divisional rivals Gala Fairydean Rovers stand in their way of a spot in the second round, while in-form Civil Service Strollers face a 400-mile round trip as they head for Golspie Sutherland of the North Caledonian League.
Bo'ness United face an even longer trek to Wick Academy, while joining them on the journey up the A9 are Dunipace, who head for Inverness and a first round clash with Clachnacuddin.
A big crowd is expected for a tasty-looking Ayrshire derby as Irvine Meadow host local rivals Auchinleck Talbot, who made it as far as the fifth round in 2018-19.
The Berwick Rangers v Gretna 2008 tie has been moved to Monday evening after being selected for live BBC Scotland TV coverage.
The first round kicked off last night with East Stirling claiming a 3-0 win over Fort William, while Cumbernauld Colts drew 1-1 with Buckie Thistle.