SNS GroupDundee United fell to a 1-0 defeat at Montrose in the Premier Sports Cup group stage.
Graham Webster pounced on a short passback from Ross Graham to net the only goal at Glebe Park in the 37th minute.
United had needed a stoppage-time penalty to beat Stirling on Saturday and now face a pressure match at home to Arbroath this weekend.
Falkirk were also on the end of an upset as Kevin Holt’s 30th-minute header earned Ayr a victory that puts Gary Naysmith’s side in command in Group G with six points. Ross MacIver missed a late penalty for John McGlynn’s side.
Kilmarnock were held to a goalless draw by Raith Rovers at Auchinleck Talbot’s Beechwood Park in their first game of the season.
Neil McCann’s side gained what could be a crucial bonus point as they emerged 4-2 winners in the shoot-out.
Aberdeen were also kicking off their campaign and Kevin Nisbet’s double earned them a 2-0 win at Highland League champions Brora Rangers. The striker converted from the spot in the 35th minute penalty before netting from close range with 15 minutes left.
Queen’s Park are ahead of Aberdeen in Group A after goals from Aidan Connolly and Jack Hamilton earned a 2-0 win at Kelty Hearts.
Charlie Reilly took his tally for the season to three goals with a double as Dundee won 5-0 at Annan.
After a goalless first half, Reilly struck twice in seven minutes – and hit the post in between – before Joe Bevan soon made it three. Simon Murray and Ashley Hay also got on the score sheet.
Kyle Connell hit the only goal as Clyde beat Airdrie in their opening game to move three points off Dundee.
First-half goals from Tyrese Sinclair and Robbie Muirhead earned Livingston a 2-0 win at Brechin in their opening match. Partick Thistle are three points above Livi in Group E after three goals in the first 16 minutes sent the Jags on their way to a 4-0 victory at Forfar.
East Kilbride opened the scoring early in the second half at Cove Rangers but were on the end of a 3-2 defeat as they failed to follow up their impressive win over Dunfermline. The Pars got off the mark with the help of an Andrew Tod double in a 4-1 victory over Dumbarton to also join St Mirren on three points in Group C.
St Johnstone made a winning start in Group F as goals from Kai Fotheringham and Ruari Paton inside half an hour saw the Perth side win 2-0 away to Lowland League champions Linlithgow Rose.
Morton’s misery continued after losing to Linlithgow as they went down 2-0 to East Fife, who scored twice in quick succession through Tom Milne and Nathan Austin.
Elsewhere, Peterhead scored three goals in eight minutes in a 3-1 win at Elgin, Jack Leitch was on target in Edinburgh City’s 2-0 win over Alloa, and Stirling came from behind to beat Spartans 3-1.
Follow STV News on WhatsApp
Scan the QR code on your mobile device for all the latest news from around the country
