bbc sports Relegated Arbroath face two cup-tie trips to Dunfermline Athletic's East End Park within seven days.
The Third Division side were on Friday drawn against the Pars in the Co-operative Insurance Cup first round.
And they will also play the First Division outfit in the opening round of the ALBA Challenge Cup, which takes place a week earlier on 24 July.
Pars director of football Jim Leishman said: "My first reaction, was 'oh no, not Arbroath again'."
However, the former Pars manager and defender recalled an entertaining encounter as Dunfermline won 2-1 in last season's Challenge Cup first round at East End.
"The bonus ball is that they are both at home," he told BBC Scotland.
"We played them last year and it was a great game.
"Arbroath played really well and made it difficult, so I am sure the manager, Jim McIntyre, will take the game serious enough and will know we have two difficult games ahead and I am really looking forward to it."
Four local derbies came out of the hat as Scotland coach Craig Levein made the draw for the Co-operative Insurance Cup's opening fixtures.
Albion Rovers host Airdrie United, Raith Rovers are at home to East Fife, Montrose make the trip to Dundee and East Stirlingshire host Alloa Athletic.
Promoted Inverness Caledonian Thistle, the only Scottish Premier League club in the draw, host Queen's Park.
Division One newcomers Stirling Albion host Forfar Athletic, while promoted Cowdenbeath are away to Clyde.
All of the 15 ties will be played on Saturday 31 July.
The draw for the Challenge Cup, which will again be sponsored by Gaelic channel BBC ALBA, will feature even more local tussles, guaranteed by the first round being regionalised.
Raith Rovers face two Fife derbies within the space of seven days, the First Division side hosting promoted Cowdenbeath as the ALBA Challenge Cup begins on Saturday 24 July.
Falkirk return to the competition for clubs outside the Scottish Premier League after their relegation and face a short trip to face Division Two champions Stirling in another dress-rehearsal for league games between the sides in the coming season.
Memories of Glasgow derbies past will be revived as Partick Thistle host one-time tenants Clyde, who have played in Cumbernauld since 1994, and the cup game has led to the cancellation of a friendly between the sides.
Morton make the trip across the Erskine Bridge to face Dumbarton.
Meanwhile, Elgin City host former Highland League rivals Ross County and Montrose drive north to take on Peterhead.
--------------------------------------------------------------------------------
Co-operative Insurance Cup first-round drawDundee v Montrose
Elgin City v Ayr United
Dunfermline Athletic v Arbroath
Annan Athletic v Partick Thistle
Stirling Albion v Forfar Athletic
Albion Rovers v Airdrie United
Ross County v Livingston
Stenhousemuir v Brechin City
Raith Rovers v East Fife
Clyde v Cowdenbeath
Peterhead v Berwick Rangers
Stranraer v Morton
Queen of the South v Dumbarton
East Stirlingshire v Alloa Athletic
Inverness Caledonian Thistle v Queen's Park
Ties to be played on Saturday 31 July
ALBA Challenge Cup first-round drawNorth/East section:
Dunfermline Athletic v Arbroath
Peterhead v Montrose
Stirling Albion v Falkirk
Elgin City v Ross County
Raith Rovers v Cowdenbeath
Dundee v Alloa Athletic
East Fife v Brechin City
Bye: Forfar Athletic
South/West section:
Partick Thistle v Clyde
Queen of the South v Albion Rovers
Dumbarton v Morton
Airdrie United v Ayr United
Stranraer v East Stirlingshire
Stenhousemuir v Annan Athletic
Queen's Park v Livingston
Bye: Berwick Rangers
Ties to be played Saturday 24 July
