Arbroath caused an upset by beating Dundee United on penalties after a 0-0 draw at Tannadice to book their place in Tuesday's draw for the last 16 of the Tunnock's Caramel Wafer Cup.
On a busy afternoon of penalty deciders, Stenhousemuir beat The New Saints after a 1-1 draw at Ochilview while Ayr United lost out to Wrexham after a 1-1 stalemate at the Racecourse Ground. It was also 1-1 between Kelty Hearts and Solihull Moors at New Central Park, with the National League side winning the shoot-out.
In the day's other cross-border ties, Airdrieonians saw off Bohemians 3-2 at the Penny Cars Stadium, last season's runners-up Connah's Quay Nomads edged out Cove Rangers 1-0 at Deeside Stadium while Glenavon were 3-0 winners away to Highland League Formartine United.
Alloa Athletic came from behind to defeat Dunfermline Athletic 2-1 at East End Park and Partick Thistle were 2-0 winners at Montrose. Inverness CT beat Morton 3-1 in the Highland capital and Clyde hit back to beat Queen of the South 3-2 at Broadwood.
Raith Rovers overcame League 1 rivals Falkirk 2-0 at Stark's Park while St Mirren Colts edged out Stirling Albion 1-0 in Paisley.
Meanwhile, East Fife went top of Ladbrokes League 1 with a 2-1 win over Forfar Athletic at Station Park.
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