Lowland League rivals Gala Fairydean Rovers and Selkirk will meet at Netherdale on Saturday, October 26.
On the same day Kelso United will entertain Duns along with an all-Berwickshire clash between Coldstream and Eyemouth United at Home Park.
Hawick Royal Albert have been drawn at home to Leith Athletic.
Vale of Leithen have been given a bye into the second round where they await the winners of the Kelso v Duns clash.
The tie of the second round is Spartans v Whitehill Welfare after both clubs received byes.
The South Challenge Cup is regionalised until the quarter finals when the all in draw will feature clubs from the South of Scotland League as well.