Tottenham Hotspur head coach Ange Postecoglou will be at risk of matching an unwanted club record when the Lilywhites face Premier League champions-elect Liverpool at Anfield on Sunday.
While the Reds only need one point on April 27 to confirm their status as 2024-25 top-flight champions, the curtain cannot come down on the domestic season quickly enough for Tottenham.
After coming agonisingly close to Champions League qualification under Postecoglou last season, Spurs have regressed remarkably in the current campaign and enter the weekend in a shocking 16th place in the Premier League table.
Such a ranking would represent Tottenham's worst league finish of all time - eclipsing their 15th-placed standing from 1993-94 - and Monday's 2-1 loss to Nuno Espirito Santo's Nottingham Forest was their 18th of the campaign.
Should Tottenham also come out on the wrong end of the scoreline on Sunday, Postecoglou will equal the record for the most amount of Premier League defeats for a single Spurs manager in one season.
Postecoglou could match unwanted 31-year feat in Liverpool fixture
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In the aforementioned 1993-94 season, Tottenham suffered 19 Premier League defeats under the tutelage of Ossie Ardiles, and they have never been beaten as many as 20 times in one campaign in the competition.
Spurs were also condemned to 19 losses in the 2003-04 campaign, but the Lilywhites had two different head coaches that year, as Glenn Hoddle was sacked in September before David Pleat took control of the reins.
The one consolation Tottenham can take heading into the weekend is that it is no longer possible for Spurs to be relegated, as they sit 16 points above 18th-placed Ipswich Town with five games left to play.
London rivals West Ham United are only one point back from Tottenham in 17th, though, and Spurs are a whopping 42 points below Liverpool, their second-highest deficit against a team whom they are facing next.
The only time Tottenham were further behind an opponent in the Premier League was in 2003-04, when they hosted an Arsenal side 43 points clear of them and witnessed their North London rivals win the league at White Hart Lane that day.
The omens are therefore extremely positive for Liverpool in that regard, and Arne Slot's men have also prevailed in two of their three meetings with Spurs so far this season, the outlier being a 1-0 loss in the first leg of their EFL Cup semi-final.
Tottenham could break club record with five-goal Liverpool thrashing
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The Reds turned the tide in that two-legged battle with a 4-0 win on home soil, though, having already triumphed in a nine-goal spectacular 6-3 earlier on in the Premier League campaign, meaning that they have struck 10 times against Spurs this term.
If Tottenham concede at least five goals to the league leaders on Sunday, they will also break an unwanted club record for the most goals shipped against a single team in one season, which was set in 2001-02.
That year, Tottenham conceded 14 times to Chelsea alone, losing 3-2 and 4-0 to the Blues in the Premier League and 4-0 in the FA Cup quarter-finals but prevailing 6-3 on aggregate in the League Cup semis.
However, Tottenham's Premier League transgressions will be forgiven if Postecoglou can lead the Lilywhites to Europa League glory, as Sunday's trip to Anfield precedes the first leg of their semi-final with Bodo/Glimt on Thursday.
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