Everton's League Cup Struggles: A History of Heartbreak
The League Cup has never been kind to Everton. Not once. Not really.
Since the competition’s birth in 1960/61, a club of Everton’s size has reached just two finals. Two. Both ended in defeat: Aston Villa in 1977, Liverpool in 1984. That Villa loss still stings – three matches needed to settle it, the third decided in the final minute of extra time. It’s the sort of heartbreak that seeps into a club’s relationship with a trophy.
The scars deepened in the 1990s. Portsmouth. Millwall. York. Oxford. Each name a reminder of nights when Everton were supposed to stroll through and instead trudged out, embarrassed and empty-handed.
Since 1984, only three semi-finals. The last one in 2016, when they somehow contrived to blow a 3-1 aggregate lead against Manchester City. A decade on, they have managed three quarter-finals, yet four of the last five campaigns have ended before the fourth round. Five penalty shootout exits in the last eight seasons have added a cruel edge to the story.
So why should this year be any different?
Cameras, pressure and a manager’s misstep
Sky’s cameras will be at Deepdale on Wednesday night for Preston v Everton. They don’t pitch up for routine second-round ties without a sniff of jeopardy. They sense an upset. Plenty of Evertonians do too, especially after David Moyes’ curious attempt to frame the season as a choice between cup progress and Premier League survival.
His comments have gone down badly. Not because supporters don’t understand priorities, but because this is a club not in Europe, with a squad that should be big enough to carry extra cup games. A proper run can light up a season, lift a dressing room, bleed confidence into league form.
Moyes knows this. Yet last season he tossed away a chance to reach the fourth round by making sweeping changes at Wolves – a side that had lost five of their opening six league games. Everton went out. The selection and the result undercut any sense of momentum.
If he repeats the trick at Preston and it backfires, the glow from that opening-day win over Crystal Palace will dim very quickly.
A very old rivalry, rarely seen
Preston v Everton is one of English football’s oldest fixtures, yet it has almost vanished from the modern calendar.
Both clubs were founder members of the Football League in 1888. Preston set the early standard, winning the inaugural league championship and the FA Cup in the same season to complete the first domestic Double. They went unbeaten in the league that year, earning the nickname “the Invincibles” – a tag only matched in the modern era by Arsenal in 2004.
Preston retained the title the following season and then finished runners-up three years in a row. After that, the honours slowed. The FA Cup arrived in 1938, but their last sustained spell at the top came in the 1950s, when they twice finished Division One runners-up. They were regulars in the top flight until relegation in 1961 – the last time Everton played a competitive game at Deepdale.
Since then? Just two meetings. Both at Goodison Park. Both 2-0 Everton wins in the FA Cup and League Cup.
Preston’s closest brushes with a Premier League return came via the play-offs in 2001 and 2005, losing in the final on both occasions. Moyes was at the heart of the first of those runs, having spent five years as a player and four as manager at Deepdale. He took them up to Division One – now the Championship – in 2000 and into that play-off final a year later.
There is another twist to this tie. Preston’s first-round win over Huddersfield was played not at Deepdale, but at Goodison Park, with their own pitch not ready. Since then, they have lost both league games, to Bolton and Wolves.
The last time these sides met came 22 years ago: a League Cup third-round tie at Goodison on 27 October 2004. Lee Carsley and Marcus Bent scored in a 2-0 Everton win. Different era, same outcome.
Moyes, rotation and a restless fanbase
Moyes is expected to rotate again. He almost has to, with a long season ahead and players needing minutes. But the memory of that Wolves defeat hangs over any team-sheet that looks too experimental.
Tyler Dibling, Carlos Alcaraz, Beto, Brennan Johnson and Jake O’Brien are all pushing to come in. On paper, that injection of fresh legs and attacking threat should be a positive. In reality, Everton supporters have seen enough weakened cup line-ups to know how quickly these nights can turn sour.
Moyes tried to explain his stance on the cups with a familiar argument – and lit a fuse.
“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?’
“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 logic is obvious. The delivery has irked fans who feel the club has treated the League Cup as an optional extra for too long. The result is a strange tension: a manager insisting he wants a run, a fanbase fearing his team selection might say otherwise.
The cameras are waiting. So are Preston, on their own ground at last, against a club with a long, unhappy history in this competition.
If Everton freeze again, this won’t just be another early exit. It will be another chapter in a story their supporters are desperate to rewrite.
