Jamie Walker nabbed the first Hearts goal of his second spell at Tynecastle - but couldn't stop the Jambos losing out on penalty kicks to East Fife.
Hearts huffed and puffed their way into the last 16 of the Betfred Cup after another toothless display against the League One side.
Walker swept the Gorgie men ahead early on but their lack of lethal edge returned to haunt Craig Levein's team as Chris Duggan levelled for the part-timers nine minutes into the second half.
They even missed out on the bonus point and a seeding for the second round as East Fife won the shoot-out 7-6 to pinch the runners-up slot from Dundee United after Sean Clare, Oliver Bozanic and Aaron Hickey all failed to convert.
The result was enough to see the Jambos top the group on nine points as East Fife, who finish on eight, wait to discover if they join Levein's men in the second round.
Elsewhere and St Johnstone 's miserable campaign came to a close with a third defeat in four outings - this time losing 2-1 to Forfar Athletic at Station Park.
Callum Tapping handed the home side a second minute lead and Ross Forbes doubled it in 53 minutes before Matty Kennedy struck a 65th minute consolation.
It means Forfar join table toppers Ross County in the second round with nine points from four games.
Motherwell maintained their perfect record in the Betfred Cup with a comfortable 4-0 win against League Two side Annan.
Stephen Robinson's side, who were already guaranteed stop spot in Group E, were never troubled by their lower league opposition.
And Liam Donnelly's double along with strikes from Liam Polworth and James Scott secured a comfortable win.
Morton could join Well in the second round after finishing second in Group E thanks to a penalty shoot-out victory over Queen of the South after a thrilling 3-3 draw.
Dunfermline made it three wins from four with a 4-0 thumping of East Kilbride at East End Park to top Group H. Kevin Nisbet hit a double, and Josh Coley and Tom Bealing also for on the scoresheet.
Hamilton Accies could qualify with Partick Thistle - who clinched top spot in Group F last night - after clinching second spot in Group F with a 3-2 win over Airdrie
Ricki Lamie and Craig Sibbald both bagged braces as Livingston cruised into the last 16 with a 5-0 demolition of Berwick Rangers, Alan Lithgow netting the other goal.
And Alloa gave themselves hope of reaching the second round with a 3-2 win at Arbroath, Alan Trouten hitting a brace after Liam Buchanan opened the Wasps' account.
In the other group matches played this afternoon Montrose won the Angus derby with Brechin on penalties after a 1-1 draw at Glebe Park.
Cove Rangers thumped Raith Rovers 3-0 at the Balmoral Stadium thanks to goals from Jamie Masson, Christian Antoniazzi and Declan Glass
Stranraer beat south west rivals Ayr United on penalty kicks at Somerset Park. Albion Rovers were too strong for edinburgh City winning 2-1 at Cliftonhill,
And Stenhousemuir finished their campaign with a 2-0 home win over Cowdenbeath.
All of which means 14 sides have now booked their place in the last 16.
Aberdeen, Celtic, Hibernian, Kilmarnock, Livingston, Motherwell, Rangers and Ross County are all seeded for the second round while Dunfermline, Forfar, Greenock Morton, Hamilton, Hearts and Partick Thistle are also in there.
Depending on tomorrow's scoreline in the Dundee vs Inverness match two of Dundee/Inverness/East Fife will make up the final two spots.
