Liverpool‘s title charge took a hit on Thursday as they lost to Manchester City, a 2-1 reverse that was the Reds’ first defeat of the Premier League season, cutting the gap between the two sides to four points.

Though Jurgen Klopp‘s side remain in pole position, the pressure is now on for a club that hasn’t won a league title since 1991.

And the Reds’ record in January under Klopp will only serve to fuel the doubts about their ability to hold on to their lead.

Klopp has 10 losses in 25 games as Liverpool manager across all competitions, form that suggests the next few weeks could be make or break for his side’s title chances.

Perhaps the German’s high-intensity pressing style takes a toll on his team during the packed calendar in December, leading to a drop in January. But whatever the reason, it’s a disconcerting record now that City have cut the gap and Tottenham are also only six points behind.

In his first season in England, Klopp oversaw losses to West Ham, Manchester United, and Stoke City in January 2016 – though the last of those came in the second leg of a League Cup semi-final tie against Stoke City that the Reds ultimately won on penalties.

The following year saw losses to Swansea and Wolves, as well as two losses to Southampton in both legs of the League Cup semi-final.

And in 2018, Klopp’s team lost to Swansea again, and followed that up with a loss to West Brom.

This month, Liverpool have an FA Cup fixture against Wolves, and then three crucial league games against Brighton, Crystal Palace and Leicester City. The latter two sides beat Man City in December to give the Reds a boost, but now loom as potential banana-skin ties.

If Liverpool are to end their long title drought, Klopp will have to resolve his January jinx.