Hearts lost to Dunfermline on penalties at Tynecastle as they exited the Betfred League Cup to increase pressure on head coach Ian Cathro.
The Edinburgh club finished a disappointing third in Group B as Dunfermline topped the section ahead of League Two Peterhead. Hearts supporters voiced their anger during the second half with a chant from the Wheatfield Stand demanding Cathro's removal. The 2-2 full-time score was not enough for progress, and Cathro suffered more public criticism after the 3-1 penalty shootout loss.
Don Cowie had put Hearts ahead on 19 minutes but Joe Cardle's quick equaliser and Declan McManus' strike early in the second half ensured a humiliating exit from the competition despite Esmael Goncalves' late equaliser.
Hearts lost 2-1 at Peterhead in this tournament in midweek and, with the league season starting next weekend, another failure amounts to a torrid beginning to the campaign. They omitted Jamie Walker from their 18-man squad due to poor performance in recent matches and training sessions. Those who did play looked bereft of guile and struggled to impose themselves.
Dunfermline, meanwhile, delivered an efficient and clinical performance to mask their status as a Championship club. They were well organised to play a counter-attacking style, a plan they executed perfectly.
Walker's absence was the talk of Tynecastle prior to kick-off but more important was the fact Hearts needed a win to guarantee progress to the Betfred Cup knockout phase. Tuesday night's shock 2-1 loss at League Two Peterhead left Cathro's side in a precarious position. The head coach started 19-year-old Jamie Brandon at right wing-back in his 3-4-3 formation and switched Michael Smith to the left.
Dunfermline were also minus a key player as striker Nicky Clark nursed an ankle injury. They brought more than 1,000 fans from Fife hoping to see them win Group B. The visitors started the match conservatively and emerged only occasionally from their shell. On 19 minutes, a quick break forward ended with winger Cardle forcing Jack Hamilton into a save from Callum Smith's cross.
If that was a warning to Hearts, they heeded it instantly. Cowie exchanged passes with Kyle Lafferty midway inside the Dunfermline half and then stepped forward to dispatch a precise low drive into the corner of the net from 20 yards. It was a lead which would last less than ten minutes, however.
Cardle controlled Kallum Higginbotham's cross on the edge of the penalty area and spun clear of Hearts centre-back John Souttar. With his left foot, the winger then arced a perfect finish away from the diving Hamilton as the away end erupted.
Prince Buaben's shot from distance was palmed away by the Dunfermline goalkeeper Sean Murdoch in the lead-up to half-time. Murdoch then had to show stunning reactions to deflect a header from his own captain, Callum Morris, on to the crossbar as it flew towards the net.
Managed by former Hearts players Allan Johnston and Sandy Clark, the East End Park side knew a draw would take them through to the last 16. To their credit, they went on the offensive and scored to take a 2-1 lead just seven minutes after the restart. Souttar was dispossessed by Smith in a dangerous area and he squared to McManus inside the Hearts box. The striker steadied himself before drilling an accurate low finish beyond Hamilton.
Hearts immediately replaced Souttar with Krystian Nowak. The young Scot was playing only his second game after six months out with a ruptured Achilles and at times looked uncomfortable. The onus for Cathro's team now was to attack in a bid to overhaul the deficit.
Murdoch made one instinctive low save from Lafferty but those in maroon were toiling to open up their opponents. When they did, Cowie's long ball to send Goncalves clear ended with the Portuguese delivering a tame cross into Murdoch's arms. Lafferty had another goalbound attempt headed clear by Nat Wedderburn as consternation grew in the stands.
Goncalves scrambled an equaliser from close range on 86 minutes after Christophe Berra nodded down a lofted free-kick. That briefly renewed hope for Hearts. Substitute Cole Stockton blasted his shot over from a corner when it looked easier to score, and with that went the chance of progress in this competition.
The 2-2 draw forced the game to a penalty shootout, which Dunfermline won 3-1. Lafferty was the only Hearts player to score out of four penalty takers - Jordan McGhee, Malaury Martin and Cowie all missed. Michael Paton, Scott Lochead and Nat Wedderburn netted for the visitors.
Hearts (3-4-2-1): Hamilton; McGhee, Souttar, Berra; Brandon, Djoum, Buaben, M Smith; Cowie, Goncalves; Lafferty.
53: Nowak for Souttar
60: Stockton for Buaben
74: Martin for Djoum
Unused subs: Noring, Smith-Brown, Randall, Currie.
Dunfermline (4-4-1-1): Murdoch; Williamson, Morris, Ashcroft, Martin; Wedderburn; Higginbotham, Paton, Wedderburn, Cardle; Smith; McManus.
66: Lochead for Smith
88: Mvoto for Cardle
Unused subs: Gill, Splaine, Talbot, Duthie.
Referee: Craig Thomson.