Everton's League Cup Journey: A Tale of Regret

Since the competition kicked off in 1960/61, it has given the club almost nothing but scars. Two finals. Two defeats. Aston Villa in 1977 – a saga that dragged to a third match, only for Everton to lose it in the final minute of extra time. Liverpool in 1984 – another chance gone.

The 1990s made it worse. Portsmouth. Millwall. York. Oxford. Names that still sting when this competition comes around. Everton have reached only three semi-finals since that 1984 loss, the most recent in 2016 when they somehow let a 3-1 aggregate lead slip against Manchester City.

Since then? A handful of brief flurries. Three quarter-finals in the last decade, but four exits at the third-round stage in the past five seasons. Five penalty shootout defeats in the last eight campaigns. Every year, the same question. Every year, the same answer.

So why should this one be different?

Deepdale under the lights on Wednesday, Sky cameras in place, the scent of an upset hanging over the night. Broadcasters can see the storyline. Plenty of Evertonians can too, especially after David Moyes’ strange attempt to frame the season as a choice between staying in the Premier League and having a proper go at the cups.

It has not gone down well.

Everton are not in Europe. The calendar is kinder than it has been in years. The squad, on paper, should be strong enough to absorb a few extra games. A cup run can do more than decorate a season; it can harden a team, carry momentum into the league, lift a club that has spent too long glancing nervously over its shoulder.

Moyes knows that. Yet last season he gambled and lost. He rotated heavily for a trip to Wolves in this competition, facing a side who had lost five of their opening six matches. It looked like a free hit at progress. Everton went out. The message that night was as damaging as the result.

His latest comments hint at a similar mindset. If he follows through, if he throws out another patched-up XI and watches them fall, it will cut into the optimism that followed the opening-day win over Crystal Palace. That fragile feel-good factor does not need another early-round exit to test it.

Old rivalry, long gap

Preston v Everton is one of English football’s oldest fixtures, a meeting of two of the game’s original heavyweights that has somehow slipped into the background of the modern era.

Both clubs were founder members of the Football League in 1888. Preston set the early standard, sweeping to the first league title and the FA Cup to complete the domestic Double. They did it without losing a single league game, earning the nickname the “Invincibles” – a tag only matched since by Arsenal in 2004.

Preston retained the league the following season and then finished runners-up three years in a row. The trophies dried up after that, with only the 1938 FA Cup added to the cabinet, but they remained a force. Twice Division One runners-up in the 1950s, regulars in the top flight until relegation in 1961.

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

Since then, just two meetings: both at Goodison Park, both 2-0 Everton wins, one in the FA Cup, one in the League Cup. Preston’s closest brushes with a top-flight return came in the play-off finals of 2001 and 2005. The first of those came under a familiar face.

Moyes spent five years as a player and four as manager at Preston, leading them to promotion to Division One – now the Championship – in 2000 and then to that play-off final a year later. Deepdale helped launch his managerial career. On Wednesday, it could turn the heat up on his current one.

There is already an Everton thread running through Preston’s current cup story. Their first-round tie against Huddersfield was played at Goodison because the Deepdale pitch was not ready. Preston won there, but their league form since has stuttered: defeats to Bolton and Wolves.

The last time they met

Everton 2-0 Preston, 27 October 2004.

Twenty-two years have passed since that League Cup third-round tie at Goodison. Lee Carsley and Marcus Bent scored the goals that night, a straightforward win in a competition that has rarely felt straightforward for Everton since.

Selection questions and simmering tension

Moyes is expected to shuffle his pack again, though the memory of last season’s early exit will make supporters wary of too many changes.

• Tyler Dibling
• Carlos Alcaraz
• Beto
• Brennan Johnson
• Jake O’Brien

Fresh legs, yes. But every new name on the teamsheet will be weighed against the risk of another stumble.

The manager’s own words have added an edge.

“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 clear. The tone has grated. Many fans heard a manager drawing lines where they wanted to see ambition, and the reaction has been sharp enough to shift the mood around this tie.

The cameras are ready. An old ground, a historic fixture, a manager caught between pragmatism and expectation. Everton’s history in this competition offers plenty of reasons to be nervous.

The question now is whether this team can finally change that story – or whether Deepdale simply writes the next painful chapter.