Hearts slumped to a shock 2-0 Premier Sports Cup defeat at Championship Falkirk as second-half goals from Ethan Ross and Dylan Tait sent their side into the quarter-finals.
Steven Naismith’s side dominated much of the first half but were wasteful with their chances, Kenneth Vargas striking the crossbar from close range with one of the most glaring misses.
That profligacy came back to haunt the visitors in the second period as Falkirk took control and made their opportunities count.
The result was already assured by the time home substitute Ryan Shanley was shown a straight red card in the final minute.
The defeat extends Hearts’ winless start to the season ahead of the first leg of their Europa League play-off against Viktoria Plzen in the Czech Republic on Thursday night.
Falkirk made just one change from the team that beat Dunfermline the previous weekend, Ross in for the suspended Callumn Morrison.
Hearts made eight changes following their 3-1 loss to Dundee. There were starts for Craig Gordon, Craig Halkett, Stephen Kingsley, Malachi Boateng, Blair Spittal, Yan Dhanda, Yutaro Oda and Liam Boyce.
Zander Clark, Daniel Oyegoke, Kye Rowles, Cammy Devlin, Jorge Grant, Barrie McKay, Lawrence Shankland and Frankie Kent made way.
The visitors started strongly and could have been in front within 30 seconds.
Oda crossed from the right for Boyce, who could not keep his left-foot effort under the crossbar.
Vargas then passed up two great chances in the space of two minutes, the Costa Rican smashing an acrobatic effort against the crossbar and then seeing a low, driven effort well saved by Nicky Hogarth.
Falkirk responded with a goal-bound effort from Gary Oliver that Gordon was able to repel before Oda ought to have finally put Hearts ahead, only to shoot straight at Hogarth, who also kept out a Spittal volley moments later.
The home side then looked certain to score shortly before the interval when Ross MacIver bore down on goal, but Gordon made a terrific save to touch the shot around a post.
It was a tetchy affair at times, with referee David Dickinson booking six players in the first half alone.
But it was Falkirk who forged in front with the first chance of the second half.
Keelan Adams crossed from the right and Ross fizzed a shot beyond Gordon from around 10 yards.
John McGlynn’s side continued to look the more dangerous and only another excellent stop from Gordon denied MacIver for the second time in the match.
The Bairns, however, got their second goal eight minutes from time when Tait threaded a shot beyond the goalkeeper to confirm their place in the last eight before Shanley was sent off for a high boot on Kingsley.