Dundee United were haunted by former Tannadice youngster Scott Allan as their miserable League Cup record continued.
United were at Hampden for last year’s Scottish Cup semi-final.
But they haven’t been in a League Cup semi-final since 2015.
That run was extended as they crashed out of the Premier Sports Cup with a 3-1 defeat to Hibernian.
Strikes from Joe Newell, Scott Allan and Martin Boyle put United three down before Peter Pawlett netted a consolation.
In a further blow, United lost both Charlie Mulgrew and Mark McNulty to injury.
Courts rang the changes from the derby-winning side with Trevor Carson, Kieran Freeman, Dylan Levitt and Nicky Clark all brought into the side.
Benjamin Siegrist, Kerr Smith, Calum Butcher and Ilmari Niskanen dropped out.
But the hosts were stunned as Hibernian took an early lead.
A defence-splitting pass from Hibernian playmaker Allan cut the home defence open and Newell swept the ball beyond Carson.
Carson then produced a stunning stop to turn over a 20-yard net-bound chip from Kyle Magennis.
Dundee United dealt Mulgrew injury blow
United were then dealt a major blow as Mulgrew was forced off injured and he must be a real doubt for Sunday’s trip to Celtic.
Mark Reynolds came on for the Tannadice side and the tide of traffic began to turn in their favour.
Peter Pawlett and Ryan Edwards both had chances to draw level before the break.
Pawlett blasted over from 15 yards and Edwards met a teasing Scott McMann cross to head wide.
United hit for three before break
HT | UNITED 0-3 HIBERNIAN
United with a mountain to climb in the second half as they head into the break with a three-goal deficit pic.twitter.com/vkNdiiAKBN
— Dundee United FC (@dundeeunitedfc) September 23, 2021
But United’s night got worse as Hibs doubled their lead through Allan.
Kevin Nisbet’s effort was partially cleared by Reynolds.
But Allan reacted to the rebound to send a composed finished beyond Carson.
It was turning into a disastrous night for United as the Easter Road side went in 3-0 up at the break.
Paul McGinn was brought down by Reynolds in the box and Boyle slotted home the penalty.
TV replays showed the spot-kick award was harsh but the hosts were left with a mountain to climb in the second half.
Martin Boyle converts from the spot to give Hibs a commanding 3-0 lead at half time! 🟢
Should it have been a penalty, though? @stephencraigan didn't think so 🤔 pic.twitter.com/xIqniaiEG8
— Premier Sports (@PremierSportsTV) September 23, 2021
The second half was as much about restoring pride as it was rescuing the tie.
And they started well as Pawlett pulled a goal back in 58 minutes.
Pawlett controlled a superb low ball from the impressive Kieran Freeman before stabbing into the bottom corner from six yards.
United were having no luck and they lost their second player of the night as McNulty pulled up with hamstring injury.
They also had a Pawlett effort wrongly ruled out for offside as Hibs marched onto their fifth consecutive semi-final.
Dundee United: Carson, Freeman, McMann, Mulgrew (Reynolds 17), Edwards, Levitt, Harkes, Fuchs (Hoti 83), Clark, McNulty (Mochrie 69), Pawlett (Appere 83). Subs not used: Siegrist; Sporle, Niskanen, Chalmers, Smith.
Hibernian: Macey; Stevenson, Porteous, McGinn, Hanlon, Boyle, Newell, Nisbet (Scott 85), Magennis (Gullan 85), Doyle-Hayes (Gogic 77), Allan (Cadden 65). Subs not used: Dabrowski; Wood-Gordon, McGregor, Doig, Mackay.
Referee – Willie Collum
