Liverpool and Joel Matip both broke a number of unwanted Premier League records in the Reds' excruciating 2-1 Premier League defeat to Tottenham Hotspur on Saturday.
Both teams headed into the blockbuster tie yet to suffer a league defeat in the 2023-24 season, although Ange Postecoglou had overseen an EFL Cup exit at the hands of Fulham.
Meanwhile, Liverpool had not lost in 19 competitive fixtures since a 4-1 beating at the hands of Manchester City in April, winning each of their last seven contests before heading down to the capital.
However, Jurgen Klopp's men were at a major disadvantage early on, as Curtis Jones was given his marching orders for a studs-up challenge on Yves Bissouma, catching the Mali man on the ankle as both men challenged for the ball.
Nevertheless, the Reds had the ball in the back of the net through Luis Diaz, but the offside flag denied the Colombian a goal that is now confirmed to have been wrongly disallowed due to "significant human error" by the officiating team.
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Just two minutes after that reprieve, Spurs went down the other end of the pitch and broke the deadlock through Son Heung-min, who side-footed home from close range after Richarlison's cutback.
The 10 men of Liverpool came out fighting, though, and Cody Gakpo levelled the scores on the stroke of half time, but an injury to the Dutchman meant that Diogo Jota was introduced for the second half.
However, the Portugal international had been on the field just shy of 25 minutes when he was also sent off for two yellow card-worthy tackles on Destiny Udogie - who appeared to trip himself up on Jota's first offence - and despite their courageous efforts, the nine-man Reds succumbed to a last-gasp own goal from Matip.
By converting Pedro Porro's cross into the roof of his own net, the Cameroonian scored the latest own goal on record in Premier League history, clocked at 95 minutes and 31 seconds.
In addition, Matip - who has kept Ibrahima Konate out of the team for the past few weeks - also now holds the unwanted honour of conceding the latest winning goal against Liverpool in the Premier League in a torrid afternoon for the experienced defender.
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Matip's record-breaking own goal is not the only undesirable statistic on Liverpool's North London notebook, as the Reds have also become the first team to pick up as many as four red cards in their opening seven games of the new season.
Klopp's side also lost Virgil van Dijk to a sending-off in the first half of their 2-1 win over Newcastle United in August, prior to which Alexis Mac Allister was sent for an early bath against Bournemouth.
Mac Allister's dismissal was eventually overturned on appeal, but Van Dijk was forced to serve a two-game ban and pay a £100,000 fine after admitting to using abusive and/or insulting language towards the officials at St James' Park.
Jones and Jota's punishments saw Liverpool break a red card record that had been held for 29 years by Leicester City, who had four dismissals in the opening eight games in the 1994-95 campaign.
The pair will now serve domestic suspensions away to Brighton & Hove Albion next week, but they will be available to face Union SG in Thursday's Europa League group-stage showdown.
However, Gakpo went down injured immediately after scoring on Saturday, and Klopp is fearful that the Dutchman may have picked up a serious problem.
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