Rangers begin their Co-operative Insurance Cup defence with a third-round home tie against Irn-Bru First Division side Dunfermline.
The Ibrox side captured the trophy with a dramatic 1-0 win over St Mirren at Hampden in March.
Celtic have been drawn at home against Inverness Caledonian Thistle, whom they beat 1-0 on the opening day of the Clydesdale Bank Premier League season.
In another all-SPL clash, Hibernian travel to Kilmarnock, managed by former Easter Road boss Mixu Paatelainen.
Aberdeen get the chance for revenge when they take on Irn-Bru First Division side Raith Rovers at Pittodrie, the Kirkcaldy men having sensationally knocked the Dons out of the Active Nation Scottish Cup after a replay last season.
Hearts, Dundee United and Motherwell face tricky away ties to lower league sides.
Jambos boss Jim Jefferies goes back to former club Falkirk, United take on Ross County, in what will be a repeat of last season’s Active Nation Scottish Cup final, while Motherwell travel north to Brechin City.
St Johnstone complete the draw with a home fixture against Queen of the South.
The ties will take place on Tuesday September 21 and Wednesday September 22.
The draw is as follows:-
Rangers v Dunfermline
Kilmarnock v Hibernian
Aberdeen v Raith Rovers
Falkirk v Hearts
Celtic v Inverness CT
Ross County v Dundee United
St Johnstone v Queen of the South
Brechin City v Motherwell