Third Time’s the Charm? - What Happened the Last Two Times Liverpool Hunted Down the Quadruple

The Dutchman's pragmatic yet attacking style has breathed new life into Anfield following the departure of fan-favorite Jürgen Klopp. But what makes this pursuit even more intriguing is how this isn’t Liverpool’s first or second go at making history.
When Arne Slot arrived on Merseyside in the summer, expectations were cautiously optimistic. By December, those expectations had turned into sheer belief. Liverpool sit comfortably at the top of the Premier League, four points ahead of Chelsea with a game in hand, and lead the newly revamped Champions League table, having already dispatched major teams like Real Madrid and Bayer Leverkusen with clinical efficiency. Their record of 11 wins from 14 league outings and six wins in as many continental fixtures tells the story of a highly cohesive and determined unit.
Key to their dominance is an electric Mohamed Salah, leading by example at 32 years old with 13 Premier League goals and another three in European competition. The Egyptian King is playing out of his skin in the hunt for a new contract - his current one expires at the end of the season - and he hasn’t been alone.
Luis Díaz has delivered some of the most vital goals in both competitions, while last summer's recruits Alexis Mac Allister and Dominik Szoboszlai command midfield battles with calm creativity. At the back, Virgil van Dijk continues to exude leadership, supported ably by Alisson's - and to a certain extent back-up Caoimhin Kelleher's - heroic performances in goal.
Slot’s approach has leaned on Klopp's high-pressing philosophies while adding his own focus on structural integrity and modern tactical nuances. Despite injuries to key players like Trent Alexander-Arnold and Diogo Jota in the campaign’s opening stretch, the team’s depth has filled gaps seamlessly. Young talents like Curtis Jones and Conor Bradley have stepped up in big moments, highlighting the holistic squad strength Liverpool are working with this season.
Their exploits have prompted online sportsbooks to slash odds on Liverpool having an epic campaign. The popular Bodog sportsbook in Canada currently makes the Reds a -135 favourite for the Premier League and a +400 frontrunner for the Champions League as well.
And yet, history whispers a warning to Kopites the world over. This is not the first time hope of an unprecedented quadruple has gripped Anfield.
Rewind to the 2021/22 season—a year when Klopp’s juggernaut came heartbreakingly close. Liverpool swept through the Carabao Cup and FA Cup, both times defeating Chelsea on penalties at Wembley. They entered the final day of the Premier League season just one point behind Manchester City and staged a thrilling comeback against Wolverhampton Wanderers. But Pep Guardiola’s side staged an iconic victory of their own against Aston Villa, rallying from two goals down with 15 minutes remaining to retain the title and once again deny the Reds.
The Champions League provided yet another painful chapter. Despite dispatching top foes like Inter Milan and Villarreal en route to the final, their dream ended in Paris with a 1-0 defeat to Real Madrid. Thibaut Courtois’ sensational performance in goal for Madrid, coupled with a Vinícius Júnior strike, sealed Liverpool’s fate.
If two years prior was agony, then last season was perhaps déjà vu. Klopp, in his final season at the club, once again masterminded a campaign to remember. The Reds advanced to the latter stages of all four competitions, rekindling talk of another quadruple bid. This time around there was a small asterisk on the trophy hunt considering the fact that they were featured in the Europa League rather than the Champions League, but still triumph on four fronts would have been an achievement of epic proportions.
Liverpool lifted the Carabao Cup after edging out Chelsea in a tense final thanks to Van Dijk's last-gasp extra-time winner. However, their hopes began to falter as soon as they had begun to arise. They were beaten in the FA Cup quarterfinals by Manchester United in one of the all-time great cup ties at Old Trafford. That triggered a downturn in form in the League and by April, Manchester City and Arsenal had established a commanding lead that Liverpool couldn’t overcome, with The Blues eventually emerging victorious for the fourth straight year.
To compound the misery, Liverpool crashed out of the Europa League in the quarter-finals against eventual champions Atalanta. The Italians shockingly won 3-0 at Anfield in the first leg thanks to a brace from Gianluca Scamacca, and while they would salvage a 1-0 win in the reverse fixture, they had to bow out after a 3-1 aggregate defeat. It was a campaign defined by inconsistency rather than dominance, and it underscored how difficult it is to chase four trophies amid a grueling fixture schedule.
What sets this season apart from the last two near-misses? For one, Slot’s adjustments have focused more on squad rotation and tactical adaptability, addressing some of the burnout evident in Klopp’s final years. Secondly, there’s an air of intrigue about how Slot has brought an unpredictable element to Liverpool’s play—a hallmark of his Feyenoord days.
Still, the road ahead is perilous. Even though Manchester City are in freefall, they still must continue to fend off Arsenal and Chelsea’s challenge in the league while surviving grueling knockout ties in Europe. The FA Cup, too, becomes a minefield as fixtures pile up post-January. Injury management and consistency will be everything.
This third attempt at the quadruple has already reignited hope and optimism around Anfield, but memories of falling short remain fresh. Whether Liverpool finally scales football’s tallest mountain or collapses under its weight is still a question no one can quite answer. What’s certain is that, once again, all eyes will be on the red side of Merseyside as they write the latest chapter of quadruple drama.