Saturday’s defeat to Livingston means Dunfermline have failed to qualify for the knock-out stages of the Premier Sports Cup for the third consecutive year.
The Pars still have Cove Rangers to play to complete Group E but the shock loss to Forfar Athletic last Tuesday has proved extremely costly.
The hat-trick of failures comes after the Fifers successfully made it through the first stage five years in a row.
On all but one of those occasions they crashed out of the competition at the next round.
The exception being the unfortunate penalty-kicks loss to eventual winners St Johnstone in the quarter-finals in 2020/21.
But, with the cup group stages coming so early in the competitive action, does it tell us anything for the Championship campaign ahead?
Courier Sport has taken a look at Dunfermline’s league record when, in contrast to this year, they have enjoyed some success in the League Cup.
1. Season 2017/18
With Allan Johnston at the helm, the Pars impressively finished top of a Group B that included Hearts, who were third.
A 6-0 victory over Elgin City was followed by a goalless draw and penalty-kicks bonus point against East Fife.
After another big win, 5-1 against Peterhead, the Fifers secured a superb 2-2 draw against Hearts at Tynecastle thanks to goals from Joe Cardle and Declan McManus.
A 3-1 success in the penalty shoot-out ensured the East End Park men finished top with ten points.
Unfortunately, they were then drawn against Rangers in the second round and suffered a chastening 6-0 hammering at Ibrox.
League: Finished 4th in the Championship
2. Season 2018/19
Again Johnston steered Dunfermline to success in the group stages, coming top of Group D above Dundee with maximum points.
A 3-0 success against Peterhead set up the Pars for a 1-0 victory over Dundee at Dens Park thanks to a Jackson Longridge strike just two minutes in.
A 7-1 thumping of Brechin City and a 3-1 win at home to Stirling Albion completed the league section.
This time, it was Hearts in the second round and Olly Lee’s solitary strike sent the Fifers out of the tournament.
League: Finished 7th in the Championship.
3. Season 2019/20
Again, Dunfermline finished top of their section, this time under manager Stevie Crawford.
A 3-2 win away to St Mirren kicked off the campaign, thanks to first-half goals from Ryan Dow, Andy Ryan and Thomas Beadling.
A 6-0 hammering of Albion Rovers followed before a surprise 1-0 defeat away to Edinburgh City.
The Fifers then clinched top spot when they eased to a 4-0 victory over East Kilbride.
Once more, the draw was unkind, however, and Celtic were the second round opponents.
But they pushed the eventual champions all the way with a Beadling strike cancelling out Mikey Johnston’s opener, only for James Forrest to win it for the Hoops in extra-time.
League: Finished 6th in the Championship.
4. Season 2020/21
With a maximum haul of points, Crawford again led Dunfermline to top spot in their group.
A 1-0 win away to Dumbarton kicked things off before a 2-0 victory over rivals Falkirk.
Then came a hugely impressive 3-0 success at Kilmarnock thanks to a goal from Euan Murray and a double from namesake Fraser.
Clyde were subsequently seen off 3-2 to send the Pars into the knock-out stages for the fourth successive season.
A kinder draw saw them squeeze past Arbroath with a 3-1 win at Gayfield to set up a last-eight clash with St Johnstone.
Goalless after 90 minutes, Iain Wilson’s strike cancelled out Adam Rooney’s goal in extra-time. But it was the Perth outfit who prevailed 4-3 in the spot-kicks decider and went on to lift the cup.
League: Finished 4th in the Championship.
5. Season 2021/22
New boss Peter Grant showed promise by leading Dunfermline through Group H as runners-up behind St Mirren.
A 4-2 win away to Partick Thistle kicked off the new regime in promising fashion with goals from Nikolay Todorov (2), Aaron Comrie and Kyle Macdonald.
Following a 1-0 defeat away to St Mirren, the Pars then hammered Dumbarton 5-1 and Stenhousemuir 4-1.
For the second time in five years, Rangers were the opponents in the second round and on this occasion the Fifers suffered a 5-0 loss at Ibrox.
Worse was to come in the league as Grant was replaced by John Hughes in the November and relegation to League One followed.
League: Finished 9th in the Championship.
