Caley Thistle will travel to Hamilton or Rangers B in the fourth-round of the SPFL Trust Trophy.
The last-16 draw took place on Tuesday and pitched the two-times winners in against opponents from their own division in Accies, or Rangers second string, who are second in the Lowland League.
Billy Dodds’ Championship side, who edged past Highland League leaders Brechin City on penalties to reach this stage, will discover who they will meet when Gers tackle Accies at Dumbarton on Tuesday November 8.
ICT have yet to face Hamilton this season, with the game being rescheduled for October 18 following the death of the Queen.
Caley Thistle beat Rangers Colts in the Challenge Cup semi-final two years ago as in a tie which saw ICT striker James Keatings sent off before his red card was lifted following widespread criticism for the decision.
The final against Raith Rovers never took place due to the pandemic and the rivals jointly shared the silverware.
Clyde clash next up for Elgin City
In-form League 2 team Elgin City, meanwhile, will host League 1 Clyde in the last 16.
The Moray men, who have knocked out Dundee United Colts, Stenhousemuir and Peterhead, are the last remaining League 2 club remaining in the cup.
Elgin’s 4-0 rout of League 1 Peterhead in the previous round will give them belief that they can progress further in the competition.
Gavin Price’s team have lost only one match in their last 10 games overall and moved up to mid-table thanks to their 5-1 rout of Annan on Saturday, inspired by four goals from striker Kane Hester.
Clyde beat Welsh opponents Caernarfon Town 1-0 in round three, but that has been the Bully Wee’s only win in six fixtures as they sit eighth in League 1, so Elgin might fancy their chances.
These two clubs have not locked horns for a few years, since Clyde were in League 2.
The full draw is – Raith Rovers v Morton, Kelty Hearts v Linfield, Queen’s Park v Montrose, Arbroath v Dunfermline Athletic or Celtic B, Alloa Athletic v Queen of the South, Falkirk v Dundee, Elgin City v Clyde, Hamilton Accies or Rangers B v Caley Thistle.
The fourth-round ties are scheduled for the weekend of December 10-11.