East Fife made Dundee pay the penalty at Bayview in a dramatic conclusion to the first game of their Betfred Cup campaigns.
Kane Hemmings had handed Dundee a first half lead but his effort was wiped out by Kevin Smith's late free-kick for the home side.
The game went to a penalty shoot-out and Scott Robinson scored the winning spot kick for the home side after Rory Loy and James Vincent had missed.
The Fifers certainly were not overawed by their Premiership opponents and took the game to Dundee during the opening exchanges.
Scott Mercer's run through on goal had to be stopped by Darren O'Dea while David Mitchell was called into action to smother a Scott Robinson free-kick.
Dundee eventually grew into the game but failed to really threaten the East Fife goal.
The visiting support, clearly expecting a more dominant showing from their side against their League One opponents, began to grow restless as Dundee were held.
East Fife were well drilled at the back and swamped their opponents each time they tried to conjure something up.
The game needed something special to open it up and it arrived with less than 10 minutes before the break when Hemmings beat Willie Muir with a dipping volley which crashed in off the post.
The quality of the Dundee frontman was evident and he went close to snatching another goal, denied only by a last ditch Jason Kerr tackle.
To their credit the Fifers continued to poke and prod as they tried to work their way back into the game.
Kyle Wilkie and Kevin Smith both tried to carve open the Dundee defence but found the visitors in a mean mood and not about to give up their clean sheet lightly.
O'Dea again had to look lively to cut out Smith's path to goal as the Fife frontman got ready to pull the trigger.
With the clock ticking down East Fife grabbed the equaliser their play had merited.
Kevin Holt pulled down Chris Duggan on the edge of the area, gifting the Fifers a free-kick.
Smith stepped up and curled a superb effort into David Mitchell's top corner.
That took the game to a penalty shoot-out and Robinson converted to earn his side an extra point.
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