Cove Rangers took Championship side Dundee to penalties before succumbing to a 3-2 loss on spot-kicks.
The Highland League champions more than held their own against a side who was in the Premiership last season, even hitting the frame of the goal in the first half through Daniel Park.
Penalties were required, with Paul McGowan scoring the decisive penalty after a goal-less 90 minutes.
They have a weekend off before travelling through to Inverness to face Caley Thistle on Tuesday.
New signing Daniel Higgins was straight into the Cove team in place of Sam Burnett, with Martin Scott back from suspension to replace Mitch Megginson.
Cammy Kerr was the first to have a sight of goal after six minutes, latching on to Jordan Marshall’s half-cleared cross to drill wide.
The Championship side tested Stuart McKenzie again inside 20 minutes, with Paul McGowan picking out Jamie Ness on the left side of the area. His low drive was gathered comfortably by the Cove goalkeeper.
Chances were coming for the hosts however, with Jack Hamilton first parrying from Scott and then gathering Daniel Park’s rebound at the second attempt. Park would find Jordon Brown just inside the area moments later and although he squeezed a shot away, Hamilton plucked it out of the air.
Former Ross County striker Craig Curran, who scored in the 3-0 win over Montrose on Saturday, ought to have added to his tally on 26 minutes, skewing over after McGowan’s header came back off the post.
Cove were the next side to hit the woodwork, with Park breaking clear after McGowan misplaced his pass. While three white shirts got back to crowd him out, he still managed to turn and get a speculative effort away that hit the bar.
Andrew Nelson, who had a quiet first period, threatened first in the second half for the away side, with an acrobatic attempt from McGowan’s cross that sailed over.
Even without leading striker and captain Mitch Megginson, Cove were presenting problems for their more illustrious opponents and were unlucky to see Harry Milne’s first-time strike fizz wide, with Jordon Foster getting a vital touch on the ball.
Nelson had another shot deflected wide by the debutant Higgins as Dundee huffed and puffed without breaking Cove’s resolve.
They blew a golden chance to score with 12 minutes to go when two substitutes, Declan McDaid and Josh Mulligan, combined to set up the youngster for a free header at the back post, but he contrived to head wide.
McKenzie was finally required with seven minutes to go as he came off his line quickly to block Nelson, after McGowan slipped him in, but Cove held firm for penalties.
Scott and Jordan McGhee both scored from the spot but Jamie Masson and Milne blasted over and Foster did the same for Dundee, before McKenzie kept out Nelson. Park and McDaid made it 2-2 before Higgins hit the bar, leaving McGowan to score the winner.