Annan Athletic will come up against their old manager in the Betfred Cup.
The Black and Golds were drawn against Clyde, where their former boss Jim Chapman left Galabank to go to last month, in Group E.
Chapman will also come up against another of his ex-clubs with Dumbarton also in the same group.
Meanwhile Carlisle United legend Peter Murphy, who was only appointed Annan's player-boss on Friday, replacing Chapman, will face Ayr United.
Murphy had spent the last three seasons with Ayr.
Scottish Premier League outfit Kilmarnock are the other side in Group E.
The venues for the fixtures are yet to be confirmed.
Last season, the Galabankies were drawn in the same group as Rangers and Motherwell.
Group E: Annan Athletic, Ayr United, Clyde, Dumbarton and Kilmarnock
Comments: Our rules
We want our comments to be a lively and valuable part of our community - a place where readers can debate and engage with the most important local issues. The ability to comment on our stories is a privilege, not a right, however, and that privilege may be withdrawn if it is abused or misused.
Please report any comments that break our rules.
Read the rules here