East Fife dumped Dundee out of the SPFL Trust Trophy on penalties after a 90-minute stalemate at Dens Park.
Both teams had chances as they went toe-to-toe in the second half, but neither could find a path to goal.
And with the match going straight to penalties at full-time, the Fifers progressed to the third round after outscoring their hosts by five spot kicks to three.
First half
Dundee’s youngsters, captained by Jack Wilkie, initially looked lively, with Fin Robertson and Ewan Murray enjoying plenty of the ball early on.
But East Fife, who matched Dundee’s three at the back formation and sought to get the ball forward as directly as possible, soon took hold of the game..
Tyler French, who took a huge step in his comeback from a broken leg by clocking up 90 minutes, was almost punished for a rusty looking pass to Ewan Murray at the edge of the Dark Blues’ box but Greig McDonald’s side couldn’t capitalise.
The Fifers went close again when Ross Philp was slipped in on goal but Dundee’s Luke Graham did well to block his attempted shot.
Then Kieran Miller saw French throw a leg in front of his 25th minute effort as East Fife pressed for the opener.
Dundee, unable to make the ball stick up top, were forced into a containing effort as their visitors controlled possession.
They did have one solid chance to break the deadlock before the interval, when Lewis Lorimer picked out Luke Graham’s back post run, only for the defender to meet it with a weak header that was easily dealt with by Reece Beveridge.
Second half
Dundee were first to threaten in the second half, when French looped a loose ball from a corner just over the East Fife bar.
Substitute Jack Healy then tested Ruaridh Lynch in the Dee goal as the visitors went straight back up the park.
Four half-time changes seemed to rob East Fife of their first half fluency, with Dundee becoming more of a force as the game matured.
But the League Two basement boys retained their attacking intent and Jude Black saw a long range effort clip the crossbar on the hour.
With just 13 minutes left, Dundee’s Finlay Allan was sent clear down the right channel and beat onrushing keeper Beveridge to the ball.
However, a deflection took the sting out of his effort, allowing Bodhi Taylor to get back and head clear.
Penalty kicks
Stewart Murdoch scores for East Fife (0-1)
Jamie Richardson effort saved (0-1)
Scott Shepherd scores for East Fife (0-2)
Callum Lamb scores for Dundee (1-2)
Jack Healy scores for East Fife (1-3)
Alex Barnett scores for Dundee (2-3)
Liam Newton scores for East Fife (2-4)
Fin Robertson scores for Dundee (3-4)
Brogan Walls scores for East Fife (3-5)
Dundee B:Lynch; French; Graham; Sweenie-Rowe; Lorimer (Lamb 62); Robertson; Murray; Wilkie; Mohammed (Barnett 72); Mutale (Allan 62); Richardson.
Subs not used: McKelvie (GK); Allan; Crowther; Craik; Mitchell; Donald.
East Fife: Beveridge; Docherty (Murdoch 81); Comeford; Newton; Philp; Miller (Healy 45); Trouten (Black 45); McManus (Walls); Hambrook; Schiavone; Nicol (Shepherd 45).
Subs not used: Fleming (GK); Murdoch; Taylor; Ramsay.
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