Hearts were held to a 2-2 draw by Petrocub of Moldova in our final European league phase match.
Results elsewhere means a draw isn't enough, with the Jambos bowing out of the UEFA Conference League.
Neil Critchley made four changes for the visit of the Moldovans as Yan Dhanda, Macaulay Tait, Lawrence Shankland and James Wilson replaced Malachi Boateng, Musa Drammeh, Kenneth Vargas and Alan Forrest.
Hearts started with intent, and had their first chance inside the opening ten minutes as Silviu Smalenea sprang into a diving save to claw a dipping strike from Lawrence Shankland away from danger.
Kye Rowles then flashed a promising header agonisingly wide on the 19th minute following a cute delivery from Dhanda at the corner. Soon after, Petrocub had their opener as they hit on the counter.
After a lengthy VAR check for a possible offside, the Moldovans' opener stood after Sergiu Platica fired Petrocub into the lead. It would be until the 34th minute that Hearts would craft something significant.
Lawrence Shankland had the ball in the net, stabbing home from close range after the Petrocub 'keeper initially fumbled, but the referee blew the whistle following a foul against the Moldovan 'stopper in the build up.
HT: Hearts 0-1 Petrocub
The Jambos fashioned two chances in quick succession after the break; Kye Rowles seeing a header float wide before a ranged strike from Lawrence Shankland at the edge of the area was deflected behind.
63 minutes saw Hearts claim the equaliser, with James Wilson showing composure beyond his years to drill a low effort beyond the keeper after Shankland did a delightful job in taking down a tricky high ball and squaring.
Hearts almost had a second moments later after Rowles saw another fine header go inches wide of the target once again. There wouldn't be long to wait for the next goal to arrive.
A dangerous cross from the right on 70 minutes saw Blair Spittal direct a free header into the corner of the net after the Moldovans failed to pick him up in the area.
There was another twist in the tale as Petrocub got a penalty ten minutes from time; a Penrice hand-ball in the area following a Moldovan attack saw Victor Mudrac send Craig Gordon the wrong way to even the score.
With six minutes of added time, Hearts couldn't find a way in, and exit Europe at the league phase.
Hearts: Gordon, Halkett (Boateng 68'), Oyegoke (Boyce 84'), Shankland ©, Devlin, Rowles, Forrest (Spittal 45'), Dhanda (Vargas 77'), Wilson, Tait (Grant 68'), Penrice
Subs: Clark, Grant, McKay, Oda, Spittal, Boateng, Boyce, Sandilands, Vargas, Salazar
