Peter Murphy's Annan Athletic have been drawn against fellow Scottish border side Queen of the South in the Betfred Cup group-stage draw.
Jack Brannan, Ayrton Sonkur, Scott Hooper, Carlisle lad Owen Moxon, Aidan Smith and Ross Fergusson are among Annan's former Queen of the South contingent although, of those, only Sonkur and Moxon have committed to stay at Galabank next term so far.
The Black and Golds, who narrowly missed out on promotion to Scottish League One last season, falling to a 2-1 aggregate loss to Clyde in the promotion play-off final, have also been drawn with Scottish Premiership side Motherwell who have ex-Carlisle keeper Mark Gillespie among their ranks.
There is also the possibility that promising Morton left-back Lewis Strapp, on loan with Annan last season, could face a quick return to Galabank with his parent club.
Scottish League One team Dumbarton make up the five in Group E in the South section for the Betfred Cup.
The fixture dates will be announced by the SPFL at a later stage.
Winger Chris Johnston and Tony Wallace (who have joined Clyde) and James Creaney and David Wilson (who have linked up with Stirling Albion) have already left Annan this summer, while right-back Hooper has signed for Peterhead, according to The Aberdeen Evening Express.
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