Montrose were dumped out of the Scottish Cup at the hands of Darvel as they slumped to a 5-2 defeat at Links Park.
Ian McShane bagged a brace alongside efforts from Cameron Eadie, Ross Caldwell and Andy Stirling as the side from the West of Scotland Football League shocked the cinch League One side.
Fellow lower-league side Drumchapel knocked out third tier Edinburgh thanks to Alex Docherty’s strike early in the second half to send them through to the third round.
The University of Stirling were victorious after extra time as Euan McGill snatched a winner with nine minutes to play to claim a 1-0 success away to Albion Rovers.
Dundee ran riot in the other game that went to extra time as a double from Derick Osei, Finlay Robertson and Luke McGowan in the extra 30 minutes blew Airdrie away 6-2 after the visitors were forced to play extra time with 10 men after Cammy Ballantyne was sent off deep into stoppage time.
Cove Rangers hammered Dunipace 7-0 while Hamilton and Dunfermline ran out 4-0 winners over East Kilbride and Forfar, respectively.
An own goal from Aaron Norris alongside strikes from Adam Brown and Matthew Yate sent Stenhousemuir through to the next round with a 3-1 victory over Formartine while Fraserburgh were dumped out 2-0 by Arbroath.
Elgin came from behind to beat Hill of Beath Hawthorn 2-1 despite playing the majority of the second half with 10 men after Angus Mailer was given his marching orders and Inverness also came from behind to beat Stirling Albion 3-2.
Mark Stowe’s strike from the penalty spot sent Linlithgow Rose through to the next round with a 1-0 win over Sauchie Juniors and Morton sent Queen of the South packing with a 4-1 scoreline.
Partick Thistle, Queen’s Park and Raith Rovers knocked out Kelty Hearts, Peterhead and Auchinleck Talbot, respectively, via 3-0 victories.
Gary Oliver bagged a brace as Falkirk hammered Wick Academy 6-0 while goals from David Wilson, Ryan Wallace and Ross MacLean handed Dumbarton a 3-1 win over Clyde.