Steven Pressley experienced a disappointing start as Dundee head coach, suffering a home defeat against Airdrieonians in the Premier Sports Cup group stage opener. The Championship side's victory was the surprise of the day.
Meanwhile, Premiership team St Mirren was held to a goalless draw by League 1 champions Arbroath and lost the bonus point in the penalty shootout. Motherwell, another top-flight team, secured an extra point by defeating Clyde in a penalty shootout after a 2-2 draw.
Ross County, recently relegated, lost their shootout after a 1-1 draw against Stranraer. In contrast, Championship winners Falkirk delivered an impressive performance, scoring seven goals against Highland League's Brechin City. Premiership teams Kilmarnock and St Johnstone also secured victories.
Group A
Falkirk's Dylan Tait scored a hat-trick in their dominant win over Brechin. Brian Graham, a summer signing, assisted Scott Arfield for Falkirk's opener, with Arfield adding a second from the penalty spot. Tait added three more goals, with Alfie Agyeman and Ross MacIver completing the scoring.
In the other Group A match, League 2's Spartans came from behind to defeat Championship visitors Queen's Park. Josh Fowler initially put Queen's Park ahead, but Bailey Dall and Cammy Russell secured the win for Spartans.
Group B
Ronan Hale of Ross County scored just before halftime against Stranraer, but Tommy Sharp equalized, leading to a penalty shootout victory for Stranraer. Partick Thistle leads the group after a 4-1 win over Edinburgh City.
Group C
Airdrieonians took an early lead at Dens Park, with Chris Mochrie's goal set up by player-manager Rhys McCabe. Dundee failed to respond, giving Airdrieonians the win. In the group's other match, Alloa Athletic defeated Bonnyrigg Rose with Luke Rankin's long-range goal.
Group D
Both Group D matches went to penalties. St Mirren drew 0-0 with Arbroath and lost 4-2 on penalties, with captain Mark O'Hara receiving a late red card. Forfar Athletic defeated Annan Athletic in a shootout after a 1-1 draw.
Group E
Relegated Hamilton Academical scored twice in the second half to defeat Stirling Albion. Connor Smith and Kyle MacDonald secured the victory. Heart of Midlothian faced Dunfermline Athletic in the evening match.
Group F
St Johnstone overcame an early deficit to defeat East Kilbride, with goals from Jamie Gullan, Adama Sidibeh, and Makenzie Kirk. Raith Rovers triumphed 5-1 over Elgin City, with Dylan Easton scoring two penalties.
Group G
Clyde took an early lead against Motherwell, but the Premiership side equalized and won the shootout for the bonus point. Greenock Morton secured a 4-2 victory over Peterhead.
Group H
Kilmarnock comfortably defeated Brora Rangers with goals from Ben Brannan and Djenairo Daniels. Livingston also won 2-1 against East Fife, despite a late red card for East Fife's Mamadou Bah.