It was a very on-brand ending given some of the visitors' recent displays, notably conceding five goals in the first 20 minutes en route to a 6-1 hammering at Newcastle.
Spurs looked to be on the receiving end of another hiding at Liverpool having found themselves 3-0 down inside 15 minutes, although the nonsense of Premier League football had other ideas.
The ever-reliable Harry Kane scored what looked like a consolation a few minutes before half-time to give Ryan Mason's side a glimmer of hope and also keep the hosts wary.
Similar to the 2-2 draw against Manchester United in midweek, a much-improved Spurs came out for the second period and started to get at a now jittery Liverpool defence.
Heung-Min Son found himself in on Alisson after a superb ball from Cristian Romero and he cut the deficit again before former Everton man Richarlison appeared to have completed a storybook comeback in the third of six stoppage-time minutes.
But like in games past at Anfield, there would be one final twist to endure Spurs would (once again) ensure their 2011 win there would remain their last.
Lucas Moura had only been on the pitch for a handful of minutes, but it was enough time for him to make a big impact on things as his careless pass was snagged by Jota, who fired in the winner for Liverpool low and hard past Fraser Forster.
It was yet another sickening moment for Tottenham in a drab season but for many, the result in Merseyside still comes as no surprise given how things in recent history have played out at one of the toughest grounds in the country.
In 2019, both teams were locked at 1-1 deep into the second half. Spurs had their chance to pull ahead on 87 minutes with Moussa Sissoko baring down on the penalty area in a two-on-one situation with Virgil van Dijk ahead of him.
The Frenchman - not exactly renowned for scoring goals - took the shot on himself and blazed his left-footed effort well over the crossbar and into the back of the stand.
A few minutes later, Spurs would shoot themselves in the foot with Hugo Lloris spilling a header onto Toby Alderweireld shortly before the ball trickled over the line in slow motion. Defeat in the 90th minute through an own goal. Ouch.
Later that year and in the following season, Spurs struck 47 seconds into the game through Kane to grab an early lead but would later see it unravel.
They could have made it 2-0 in the second half after Son rounded Alisson but his effort smacked off the crossbar - a moment that would end up being a turning point in proceedings.
Jordan Henderson would equalise moments later before Mohamed Salah would convert what would be the winner via the penalty spot after Serge Aurier fouled Sadio Mane.
One year later with a Covid-reduced crowd, Spurs squandered a series of second-half chances on the counter-attack with Steven Bergwijn hitting the post, poking an effort wide and Kane missing a point-blank header.
They would then go on to lose the game by conceding in the last minute again, this time to a Roberto Firmino header after some slack marking from a corner - another game that got away from them.
A relatively low drama 1-1 draw - which Antonio Conte's Spurs were pegged back in - then followed which brings us up to Sunday's pulsating encounter.
Tottenham's woeful start required them to try and dig themselves out of yet another hole but you also wonder, "What could have been?" given the number of flashpoints that would follow.
It already looked to be one of those days for Spurs when Son and Romero struck both posts within seconds of each other and had penalty appeals waved away after Ibrahima Konate grappled with Richarlison.
But the biggest kick in the teeth was the match-winner coming courtesy of Jota, who looked fortunate to escape an earlier red card after catching Oliver Skipp in the head with a high boot.
There are fine margins in football and unfortunately for Spurs, they have recently found themselves to be on the wrong side of that against Liverpool at Anfield.
