Jurgen Klopp faces an unwelcome milestone with Liverpool, while Arne Slot receives a warning about Manchester United’s most recent victory at Anfield.

Jurgen Klopp admitted it was difficult to stay positive after Liverpool’s loss to Manchester United in January 2016, but with hindsight, he might have taken comfort knowing what lay ahead. Nearly nine years on, that victory remains United’s last at Anfield. Since then, they’ve only scored once—a Jesse Lingard goal—while Klopp endured his first Anfield defeat as Wayne Rooney silenced the Kop.

Just two months into his Liverpool tenure, Klopp faced a United side managed by Louis van Gaal, who engineered another tactical triumph. Back then, Anfield was far from the fortress it would become under Klopp, and United capitalized, with Rooney scoring their only shot on target. It was also the first time Liverpool had failed to score at home under Klopp, despite fielding a front three of Roberto Firmino, James Milner, and Adam Lallana.

In the weeks leading up to the match, United had struggled, winning just two of their previous 11 games. Meanwhile, Liverpool were in strong form, defeating eventual champions Leicester City, thrashing Manchester City, and drawing against Arsenal in a thrilling six-goal encounter. Despite entering as favorites, Liverpool fell short. “We lost a game we should not have lost,” Klopp reflected afterward.

Van Gaal’s victory marked his second consecutive win at Anfield and his fourth straight over Liverpool, cementing a perfect record against their arch-rivals. For all the criticism he faced at Old Trafford, these victories earned him considerable credit. Fast forward to this weekend, parallels can be drawn as United, now led by Ruben Amorim, enter Anfield with a poor run of form—three wins in their last 11 and five defeats in their last six. In contrast, Liverpool are unbeaten in 11 matches, with eight wins and three draws.

Arne Slot, preparing for his first taste of the Liverpool-United rivalry at Anfield, already boasts a 3-0 victory at Old Trafford this season. However, keeping United from securing a shock win—a feat Klopp initially failed to achieve—will be a challenging task. Amorim’s United will likely need to replicate Van Gaal’s smash-and-grab approach, as Liverpool are expected to dominate.

Slot, who exposed United’s weaknesses earlier this season by exploiting their high full-backs, now faces a different challenge against Amorim’s system. Although Amorim has struggled recently, his style of play has already been exploited by multiple teams. Despite United’s struggles and even talks of relegation, surprises at Anfield are not unheard of. Van Gaal, though unpopular at times, proved that an away win over Liverpool can buy significant goodwill.

Slot has the upper hand heading into Sunday, but he must ensure United don’t pull off an unexpected upset

at Anfield.