Drawing Rangers in the quarter-final of the League Cup has never been a successful route for Dundee.
That’s now six times they have met the Gers in the final eight of the competition and six times they’ve been knocked out.
Rangers won in 1960, 1986, 1988, 2009, 2022 and now 2024.
This time around the writing was on the wall early on as the Glasgow side started fast, netting after 18 minutes through Cyriel Dessers.
Dundee, though, appeared to weather the storm as the half wore on only to see the game get away from them shortly after the break with a James Tavernier penalty.
Dessers would add his second with 24 minutes to go and the game was done.
What can we take from the contest from a Dundee point of view?
Courier Sport was there to analyse all the action.
Penalties
Two defeats on the bounce, two weeks running where penalties have been conceded around half-time. A really damaging time to do so.
Both given away by challenges that were needless as well.
This time it was Mo Sylla blotting his usually blank copybook by hauling down Gers striker Dessers from a corner kick.
Sylla won the ball but hands all over Dessers was asking for trouble.
With Tavernier’s finish the cup-tie was all but over just moments into the second half.
Self-inflicted problems have been a big problem this season.
Only in the most recent two matches have they brought defeats but concern is growing.
Both boxes
Against Premiership opposition Dundee have now conceded 13 goals in six matches. That’s far too many to be successful.
When you’re scoring at least two goals in every game you can still pick up results with a leaky backline.
But that’s two blanks in a row now. Dundee haven’t scored since August.
They really should have netted at least one on this occasion.
Jack Butland pulled off two excellent saves to deny Simon Murray and Scott Tiffoney.
Murray’s would have put a bit of pressure on the home side after a shaky few weeks by making it 2-1.
Seb Palmer-Houlden also had the big opportunity to make it 2-1, getting his free header from Lyall Cameron’s superb cross all wrong.
Seconds later it was 3-0 and the game was well and truly done as a contest.
That’s the margins at places like Ibrox. When a chance comes you have to take it.
Youthful Dee
Five of the starters for Dundee at Ibrox were 22 or under.
And another four came off the bench. This is a very young side.
A lot of quality but overall a lot of inexperience with plenty getting their first taste of playing away at Rangers.
Early on there was a rabbit in the headlights look about one or two as the Ibrox side absolutely dominated the opening stages.
But they got through that and their quality began to emerge.
Despite playing just two halves of football for Dundee, Seun Adewumi looks to have a big future ahead of him.
Billy Koumetio, Ziyad Larkeche and Sammy Braybrooke all had their moments throughout.
All, too, will be far better for this experience which bodes well for the future at Dens Park.
However, the youngsters need to learn quickly – results need to start coming.
Silver lining
Though there is frustration at key parts of this performance and the disappointment of going out of the League Cup there is a silver lining for the club.
Getting to this stage and playing away at a big stadium brings in good, hard cash.
Cash than can help the team improve on this stage.
Going out at this stage brings prize money of £100,000 plus there’s £30,000 for the match broadcast live on Premier Sports.
Also, after the home club takes 15% of the gate receipts for operational costs the remaining 85% of the gate receipts are split between the two clubs.
So 42.5% of the money from the 33,665 attendance will be heading Dundee’s way.
That will be well over £250,000 just for competing.
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