Everton's League Cup Struggles: A History of Heartbreak

The League Cup has never really liked Everton. The feeling, you suspect, is mutual.

Since the competition began in 1960-61, Everton have only made it to two finals. Two. For a club of their size, that record is astonishing. And not in a good way.

The first came in 1977, when they were dragged through a three-game epic with Aston Villa, only to lose the decisive match in the final minute of extra time. The second arrived in 1984, a derby against Liverpool that also slipped away. Two trips to the showpiece, no trophy, plenty of scars.

The 1990s only deepened the gloom. Portsmouth. Millwall. York. Oxford. A roll call of lower-league exits that still makes Evertonians wince. Since that 1984 final, they have reached the semi-finals just three times. The last of those, in 2016, ended with them tossing away a 3-1 aggregate lead to Manchester City. Another what-if, another missed chance.

The decade since has not offered much comfort. Three quarter-finals, yes, but in four of the last five seasons they have not even made it past the third round. Five penalty shootout defeats in their last eight ties underline a simple truth: this cup has been merciless.

So why should this year feel any different?

Cameras, pressure and a manager’s misstep

Sky’s cameras will be at Deepdale on Wednesday night for Preston v Everton. They do not turn up for routine away wins. They turn up when they sense jeopardy, when the script hints at an upset.

Everton fans sense it too, not least after David Moyes’ curious attempt to frame the season as a choice between staying in the Premier League and progressing in the cups. His comments have gone down badly. Supporters have heard variations of that argument for years, and all they have to show for it is survival and a dusty trophy cabinet.

The logic feels flimsy. Everton are not in Europe. The fixture list is manageable. The squad, on paper, is big enough to handle a few extra midweek games. A proper cup run can lift a club, energise a stadium, bleed confidence into league form. That is the theory, anyway.

Last season, Moyes seemed to ignore it. He made sweeping changes for a League Cup tie away at Wolves, a side who had lost five of their opening six games. Everton went out. A clear route to the fourth round was tossed away, and with it a chance to build something beyond the weekly grind of the league.

His latest remarks suggest he may again be tempted to rotate heavily. If that leads to another early exit, the glow from the opening-day win over Crystal Palace will dim quickly. The feel-good factor has only just returned to Goodison. It would not take much to puncture it.

Deepdale, history and an old connection

Preston v Everton is one of English football’s oldest fixtures, born in 1888 when both clubs helped form the Football League. Yet in the modern era it has become a rarity, almost a relic.

Preston were the original powerhouse. They won that first league title and the FA Cup in the same season, completing the first domestic Double. They went unbeaten in the league, earning the nickname the “Invincibles” – a label only matched in the top flight by Arsenal in 2004.

They retained the title the following year and then finished runners-up three seasons in a row. After that, the trophies dried up. A lone FA Cup in 1938 stands as their last major honour. Still, they remained a top-flight presence for decades, finishing Division One runners-up twice in the 1950s and staying among the elite until relegation in 1961.

That 1961 season was the last time Everton played a competitive match at Deepdale.

Since then, the clubs have met just twice, both at Goodison Park. Both ended in 2-0 wins for Everton, in the FA Cup and League Cup respectively. The most recent came in October 2004, a League Cup third-round tie settled by goals from Lee Carsley and Marcus Bent. Twenty-two years have passed since that night. The context, for both clubs, is very different now.

Preston’s closest brushes with the top flight since relegation have come via the play-offs. They reached the final in 2001 and 2005, losing both. The first of those runs was overseen by a familiar figure: David Moyes.

Moyes spent five years as a player at Deepdale before returning as manager. He led Preston to promotion to Division One – now the Championship – in 2000, then to that play-off final a year later. His reputation was forged there, his managerial career launched on that old ground. On Wednesday, he walks back into a stadium that once felt like home, now as the man trying to avoid becoming the story.

There is already an Everton twist to Preston’s current cup campaign. Their first-round win over Huddersfield was played at Goodison Park because the Deepdale pitch was not ready. Since then, though, their league form has stuttered: two games, two defeats, against Bolton and Wolves.

On paper, that should make Everton favourites. On nights like this, paper counts for very little.

Selection roulette and a restless fanbase

Moyes is expected to shuffle his pack again. He almost has to. The trick is not to go too far.

Supporters will be on edge if the team sheet resembles last season’s ill-fated rotation at Molineux. This time, at least, he has options that feel like genuine changes rather than gambles.

Tyler Dibling, Carlos Alcaraz, Beto, Brennan Johnson and Jake O'Brien are all pushing to come into the side. Some bring energy, some bring physicality, some bring the kind of direct threat that can quieten a restless away crowd. Pick the right blend and Everton should have enough. Pick the wrong one and Deepdale will sense blood.

Moyes insists the premise of the debate is flawed.

“This is a question every journalist asks every manager and, in some ways, I think: ‘Are those journalists dead stupid? Do you think none of the managers want to win the cups?’” he said.

“If I asked you: ‘Would it be more important than staying in the Premier League?’ – what would your answer be? Your answer will half answer your own question.

“I can't think of any manager who wouldn't want a good run in a cup competition.”

The words are clear. The reaction less so. Many Everton fans have interpreted them as another signal that the cups will always sit behind survival on the priority list. That reading has clearly irritated Moyes. The problem for him is that, at Everton, the patience for that argument is running out.

The League Cup has bruised this club for decades. The fear, as they head to Deepdale under the glare of live TV, is that it is about to do it again.