The 25-year-old trophy drought weighs heavy on Evertonian shoulders, with the League Cup in all its various guises being a particular source of heartbreak and disappointment over the years.
The Toffees have never won the competition, finishing runners-up twice, and have reached the semi-finals just twice in the last 30 years.
Winning on Wednesday would be a mini-slice of history in itself.
The competition is much-maligned, particularly by the bigger sides, but Everton cannot afford to be picky after so long without silverware.
Carlo Ancelotti has already said he will name his strongest side possible and I’m certain Goodison would have been packed to the rafters had we been in normal times.
As it is there will once again be 2,000 lucky supporters at the Grand Old Lady.
The Toffees are one of only four Premier League sides permitted to have fans, though with Covid infections rising again across the country I wonder how long it will be before all games are sent behind closed doors again.
Until that happens, the Toffees need to use those fans to their advantage.
Victory would secure a last four tie at the start of next month, which has been switched to one-leg rather than its usual two to account for the busy schedule.
The final, originally due to take place at the end of February, has been moved to the end of April to increase the chances of fans being allowed in.
But that’s for the future. One step at a time eh, Blues?
Manchester United are the only side in the top six to have beaten Everton so far this season, with the Red Devis easing to a 3-1 victory in November.
They return to Merseyside on the back of successive victories that has lifted them above the Toffees in the table on goal difference and into third.
Yet, despite that healthy league position, they never seem more than one or two games away from a crisis, with Ole Gunnar Solskjaer’s position regularly in peril.
Their ropey European form, which saw them knocked out of the Champions League, and some shaky results at Old Trafford have largely been responsible for that.
But their results on the road have been outstanding, winning every domestic away match this season.
This competition is likely to be way down their priority list but Solskjaer is still hunting a first trophy at Red Devils boss.
He has already spoken of the importance of gaining that winning habit, gleaned from his hugely successful playing days.
Any suggestion he is going to take this game lightly looks misguided.
Everton 1-3 Manchester United, November 7 2020
You only have to go back a few weeks for the last meeting between the sides, but it was a disappointing afternoon for the Blues. Bernard fired Everton in front but Bruno Fernandes scored twice before half-time, with submitted Edinson Cavani sealing the match late on.
Arsenal (H) Won 2-1
Leicester (A) Won 2-0
Chelsea (H) Won 1-0
Burnley (A) Drew 1-1
Leeds (H) Lost 1-0
Leeds (H) Won 6-2
Sheff Utd (A) Won 3-2
Man City (H) Drew 0-0
RB Leipzig (A - Champions League) Lost 3-1
West Ham (A) Won 3-1
Ancelotti has confirmed that James Rodriguez misses out again as he continues his slow recovery from a calf injury.
Andre Gomes could return after he missed the win over Arsenal with a minor hamstring problem.
Lucas Digne, Allan and Fabian Delph are still sidelined.
What they said
Everton boss Carlo Ancelotti: “We are here [in the quarter-final] and want to fight for this.
“It is an important game in the quarter-final of an important competition Everton never won.
“We are not so far from achieving this and are in a good moment.
“But we are going to play against a really tough opponent who beat us here a few weeks ago.
“It is a great opportunity to show the momentum we have.”
Man Utd boss Ole Gunnar Solskjaer: “We want to improve every season and to improve from last year is to get to the final and when you get to the final there’s only one thing that matters and that’s to lift the trophy.
“I remember myself winning my first trophy, even towards the end of my career I think it was Patrice Evra and Nemanja Vidic’s first trophy in the Worthington Cup, 2006 was it? I think that was their first trophy, and it does give something to a team, so we are desperate to get our hands on a trophy.
“These players are desperate to learn how to win.”
Even before this unusual season started I felt the EFL Cup was something for Everton to aim for. They have shown already this season that they are good enough to beat the best teams in the country, so Wednesday’s challenge should hold no fear.
I get the argument that a top four place should be the priority. But, for me, ending that trophy drought, and the pressure that will instantly release from the club, is more important.
It’s high time Everton grasped one of these opportunities and not hurl another log on the dumpster of regret.