Everton's League Cup Struggles: A History of Disappointment

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

Since the competition kicked off in 1960/61, Everton have reached just two finals. Two. For a club of their size and history, that record still jars. The first came in 1977, a marathon against Aston Villa that dragged into a third match and was finally lost in the last minute of extra time. The second, in 1984, went to their neighbours Liverpool.

Nothing since. Just a long trail of stumbles and self-inflicted wounds.

The 1990s were especially bleak. Portsmouth. Millwall. York. Oxford. Names that still make Evertonians wince when the League Cup draw appears on screen. Nights when the club managed to turn a straightforward tie into a cautionary tale.

Since that 1984 final, Everton have made the semi-finals only three times. The most recent, in 2016, still hurts: a 3-1 aggregate lead against Manchester City, squandered. In the decade that followed, three quarter-finals offered a hint of progress, but the pattern quickly reasserted itself. Four of the last five seasons have ended at or before the third round. Five exits on penalties in the last eight campaigns. The competition keeps finding new ways to torment them.

So why should this season be any different?

Cameras, pressure and a manager’s dilemma

Sky’s cameras will be at Deepdale on Wednesday night. That alone tells you the mood around this tie: the broadcasters can smell an upset. Plenty of Everton fans can too, especially after David Moyes’ recent comments that framed the season as a kind of trade-off between cup progress and Premier League survival.

For a club not burdened by European football, that logic is hard to swallow. Everton’s squad should be deep enough to cope with a few extra midweek fixtures. A cup run can do strange things to a season, injecting belief, rhythm and edge into league performances. The idea that you must choose one or the other has gone down badly.

Moyes has been here before. Last season he heavily rotated for a League Cup tie away at Wolves, a side who had lost five of their first six games. Everton went out. It felt like a wasted chance, a self-inflicted ceiling on what the season could become. His latest remarks hint at a similar calculation now. Another early exit, and some of the optimism generated by the opening-day win over Crystal Palace will drain away very quickly.

That is the tension hanging over this trip to Preston. Not just the risk of a cup upset, but the sense that the manager’s own words have raised the stakes.

Preston, Deepdale and a very old rivalry

Preston v Everton is one of English football’s oldest fixtures, but it belongs to another era. Since colour television arrived, it has barely been seen.

Both clubs were founder members of the Football League in 1888. Preston set the early standard, winning the first league championship and the FA Cup in the same season to claim the original domestic Double. They went unbeaten in the league that year, earning the nickname the ‘Invincibles’ – a title only matched in the modern era by Arsenal in 2004.

Preston retained the league the following season and then finished runners-up three years in a row. The glory years faded after that. A solitary FA Cup in 1938 stands as their last major trophy, though they pushed hard in the 1950s, twice finishing Division One runners-up and spending most of that decade in the top flight.

Relegation in 1961 changed everything. That was the last time Everton played a competitive match at Deepdale.

Since then, the fixture has almost vanished. Just two meetings in more than six decades, both at Goodison Park, both 2-0 wins for Everton – one in the FA Cup, one in the League Cup.

Preston’s closest brushes with a top-flight return came in play-off finals in 2001 and 2005. The first of those had a familiar face in the dugout: David Moyes. Before he became synonymous with Everton, he spent five years as a player and four as a manager at Deepdale, guiding Preston to promotion to Division One – now the Championship – in 2000 and then into that play-off final a year later.

There is another twist to this tie. Preston’s first-round win in this season’s League Cup came at Goodison Park, not Deepdale, because their pitch was not ready. They beat Huddersfield there, borrowing Everton’s home. Since then, though, the league campaign has stuttered: defeats to Bolton and Wolves have checked their early momentum.

The last time they met

You have to wind back 22 years for the last competitive meeting. On 27 October 2004, Everton beat Preston 2-0 in a League Cup third-round tie at Goodison. Lee Carsley and Marcus Bent scored the goals. It was a straightforward night, the kind that has become strangely rare for Everton in this competition.

Deepdale under the lights, with cameras rolling and a manager under scrutiny, promises something different.

Moyes’ selection gamble

Team selection will be watched closely. Moyes is expected to rotate again, but the memory of last season’s changes still lingers. Supporters want freshness, not a scratch XI that invites trouble.

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

are all pushing to come into the side. There is enough quality there to win this tie without ripping out the spine of the team. The question is how far Moyes goes.

His own words on the cup-versus-league debate have not helped his cause.

“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 logic is clear. The tone has grated. Many supporters have interpreted it as a softening of ambition, a pre-emptive defence if things go wrong. Instead of lowering expectations, it has sharpened them.

Because if you talk about priorities, you have to live with the consequences. Lose at Deepdale, and this will not just feel like another League Cup exit. It will feel like a choice confirmed.

And that is why, for all the history and all the scars, this tie carries an edge that Everton cannot afford to ignore.