Everton and the League Cup: A History of Heartbreak

Since the competition’s birth in 1960/61, it has given the club just two finals and two heartbreaks – Aston Villa in 1977, Liverpool in 1984. That Villa defeat needed three matches and was settled in the final minute of extra time. It fits the pattern. When this club goes deep in this tournament, it tends to end badly.

The 1990s made things worse. Portsmouth. Millwall. York. Oxford. A grim roll call of lower-league exits that still sting supporters of a certain age. The scars have never really healed.

Semi-finals? Just three since 1984. The last, in 2016, saw Everton somehow squander a 3-1 aggregate lead against Manchester City. In the decade since, they’ve managed three quarter-finals but have failed to get past the third round in four of the last five seasons. Five shoot-out defeats in their last eight ties add a fresh layer of cruelty.

So why should this year be any different?

Deepdale under the lights, Sky cameras in place, Preston sensing a chance. It has all the ingredients. The broadcasters clearly fancy the upset. After David Moyes’ strange attempt to frame cup progress and Premier League survival as some sort of either-or choice, plenty of Evertonians do as well.

The logic says it shouldn’t be like this. Everton are not in Europe. The squad, on paper, is big enough to handle extra cup games. A run in this competition can build momentum, give fringe players rhythm, spill confidence into the league. This should be an opportunity, not a dilemma.

Yet last season hangs over this tie. Moyes effectively tossed away a route to the fourth round when he rotated heavily for an away trip to Wolves, who had lost five of their first six league games. Everton went out. The message was clear, and not in a good way. His latest comments hint at the same cautious approach, and another early exit would puncture the optimism created by that opening-day win over Crystal Palace.

Old rivalry, new stage

Preston v Everton is one of English football’s oldest fixtures, but it belongs more to sepia photographs than HD coverage. Both clubs were founder members of the Football League in 1888. Preston set the early standard, winning the first league title and the FA Cup to complete the inaugural Double. They went the entire league season unbeaten, earning the nickname the “Invincibles” – a tag only matched since by Arsenal in 2004.

Preston retained the league the following year and then finished runners-up three seasons in a row. After that, the honours slowed. The FA Cup in 1938 stands as their last major trophy, though they twice finished Division One runners-up in the 1950s and were a regular top-flight presence until relegation in 1961.

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

Since then? Just two meetings, both at Goodison, both 2-0 wins for Everton in the FA Cup and League Cup. 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.

Preston have flirted with a Premier League return without quite making it. They reached the play-off final in 2001 and 2005, the first under a young David Moyes. His connection to Deepdale runs deep: five years as a player, four as manager, promotion to Division One (now the Championship) in 2000 and a play-off final a year later. He knows exactly what this club and this ground can generate when they sense an upset.

There is already a neat twist to this season’s story. Preston’s first-round win over Huddersfield came at Goodison Park because the Deepdale pitch was not ready. Since then, they have lost both league fixtures, to Bolton and Wolves, and arrive in need of a spark. Everton, unintentionally, have already played a part in their cup run. Now they must try to end it.

Moyes, rotation and a nervous fanbase

Team selection will be watched closely. Moyes is expected to shuffle his pack again, but the memory of last year’s Wolves defeat means supporters will be wary of too much change.

Tyler Dibling, Carlos Alcaraz, Beto, Brennan Johnson and Jake O’Brien are all pushing to come into the side. Fresh legs, different profiles, a chance for some to stake a claim. It can work. It can also go horribly wrong if the balance is off and the home side sense vulnerability.

Moyes bristled when asked about his priorities.

“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 words are one thing; the choices on the teamsheet are another. The reaction to those comments – or at least the way they’ve been interpreted – has clearly irritated supporters. Many feel he has turned a simple demand into a false debate. That frustration only cranks up the pressure to avoid another early exit.

Everton’s history in this competition, the manager’s past at Preston, the TV cameras waiting for drama – it all points to one question as the teams walk out at Deepdale: is this the night the League Cup finally gives them something other than regret?