Hearts exited the Premier Sports Cup at round two following a penalty shootout defeat to St. Mirren in Paisley.
Derek McInnes opted for an attacking line up at the SMiSa Stadium; Pierre Landry Kabore was in from the start for his Hearts debut, supported by Lawrence Shankland and Alexandros Kyziridis - with a midfield of Cammy Devlin, Tomas Magnusson, and Oisin McEntee anchoring.
It was all St. Mirren during the opening exchanges in Renfrewshire, Craig Halkett and Harry Milne both supplying vital blocks to deny early Buddies chances as Hearts weathered the storm.
The first clear cut chance came after 12 minutes as Zander Clark made a smart stop at his near post to deny Mikael Mandron; the Frenchman pouncing on a deflected forward ball to test Hearts' mettle.
The Jambos couldn't quite get their foot on the ball, with St. Mirren threatening again after 25 minutes as Killian Phillips screwed a powerful daisy cutter at Clark, with the Hearts stopper diving into action to deny him.
Hearts had their first opportunity on the half-hour mark; Harry Milne's delivery from the corner found Craig Halkett in space - with the centre-back sending a bullet header whizzing just over the crossbar.
St. Mirren claimed the lead after 34 minutes via a well worked set play routine. Phillips drilled the ball crossfield before it was sweeped into the path of Alex Gogic, with the midfielder swiping home from close range to make it 1-0.
HT: St. Mirren 1-0 Heart of Midlothian
St. Mirren emerged from the traps with the bit between their teeth, and registered their first chance of the half after 50 minutes as Killian Phillips ripped another stinging volley at goal from distance, Clark again throwing himself down to push it away.
Hearts kept at it, and the introduction of subs to the game certainly provided the Jambos with fresh impetus; Claudio Braga's mazy run after 67 minutes culminating in a stop from Shamal George in the Buddies goal.
The Portuguese marksman went close again after 73 minutes, trying his luck with a spectacular effort from distance that forced another stop from George as Hearts continued the search for an equaliser.
After 79 minutes, Hearts got onto level terms. Another Milne delivery from the corner found Oisin McEntee unmarked at the back post - the Irishman peeling away from his marker and planting a great header beyond George.
Hearts maintained their press, but couldn't find a way through as the game went into extra time to be decided.
After two periods of extra time with no goals, Hearts went to penalties, with St. Mirren going through with a 5-4 win after an unfortunate penalty save for Claudio Braga's effort.
St. Mirren: George, Richardson (Sobowale 83'), O’Hara, Mandron (Mooney 83'), Ayunga (King 90'), Gogic, Freckleton, Fraser, John (Tanser 45'), Baccus (Idowu 83'), Phillips (Dijksteel 105')
Subs: Mullen, Tanser, King, Idowu, Calvin, Dijksteel, Sobowale, Taylor, Mooney
Hearts: Clark, Kent, Halkett (Forrest 74'), Shankland, Kabore (Kabangu 45'), Devlin, Milne (Kingsley 105') , Findlay, Magnusson (Baningime 45'), McEntee (Steinwender 97'), Kyziridis (Braga 45')
Subs: Stone, Kingsley, Baningime, Kabangu, Braga, Steinwender, Spittal, Forrest, Wilson
Hearts Debut: Pierre Landry Kabore
