Hearts will seal top spot if they avoid defeat at East Fife but a victory for Darren Young's team at Bayview would see them leapfrog their Premiership opponents. Stenhousemuir host Cowdenbeath in the day's other game.
Ross County are already through to the last 16 as group winners with a 100% record and Forfar Athletic could join them if they beat St Johnstone at Station Park. Brechin City and Montrose meet in an Angus derby at Glebe Park.
Hibernian lead the way and face Elgin City at Borough Briggs on Friday night, live on BT Sport. Elgin will join Hibs on the eight-point mark if they pull off a shock win. Arbroath are second and could qualify if they beat Alloa Athletic at Gayfield.
Cove Rangers and Raith Rovers meet at the Balmoral Stadium on Saturday but both are already out. Inverness CT and Dundee are tied at the top on seven points as they prepare to go head to head at the Kilmac Stadium at Dens Park on Sunday, live on BT Sport at 3.00pm.
Motherwell have a 100% record and a need a draw at home to Annan Athletic to be certain of top spot. Morton, who are second, host Queen of the South at Cappielow with both still hoping to progress.
Partick Thistle beat Clyde in midweek to win the group. The big game on Saturday sees Lanarkshire rivals Airdrieonians and Hamilton Accies clash at the Penny Cars Stadium while Queen's Park and Clyde meet at the same venue on Sunday.
Livingston top the section and will expect to beat struggling Berwick Rangers at the Tony Macaroni Arena. A home win for Ayr United against Stranraer should also be enough to take Ian McCall's men through.
A draw at home to East Kilbride would take Dunfermline Athletic through but if the Lowland League champions win at East End Park they will top the section. League 2 rivals Albion Rovers and Edinburgh City meet at the Reigart Stadium in the other game.