Playing against Liverpool is never easy, even when it comes in a competition where a lot of clubs tend to heavily rotate in the earlier rounds.
Tottenham took the initiative against Liverpool
For example, the Reds had five players in their starting XI who would normally be on the subs bench, and even Roberto De Zerbi had made six changes to the side that beat the Addicks.
Despite those changes, both teams were still strong enough that you couldn't accuse either of putting out subpar XIs.
The visitors were brighter in the opening exchanges, and with a little more luck, Spurs might've opened the scoring thanks to either Mohammed Kudus or Lucas Bergvall.
The latter had the first on-target effort after 10 minutes, and really should've scored from it rather than playing it against Giorgi Mamardashvili's outstretched legs.
Mac Allister strikes
Although Liverpool took the lead through a brilliant Alexis Mac Allister strike, the ease with which the Lilywhites were knocking the ball about led to Andoni Iraola being a lot more animated than usual on the sidelines.
Only Mathys Tel and Kudus can be disappointed with their distribution, with many Tottenham players posting figures in the high 80 per cent or low 90 per cent range.
There was, however, a tendency to overplay their passing game at times.
Whilst 'De Zerbi ball,' for want of a better phrase, has long been lauded, and when it's in full flow it really is a joy to watch, when Martin Dubravka kept getting his own defenders in trouble just to play out from the back, one could legitimately ask the question as to why the manager didn't change things up a bit.
Tosin, a colossus at the back for Spurs
Going a goal down only seemed to fire the visitors up, and the next four efforts at goal all came from Tottenham players.
Even centre-back Tosin Adarabioyo got in on the act with a header that was blocked, one of three chances he had on goal in the game - only Mac Allister had more (four).
Tosin was also a colossus in a defensive sense, too, winning 10 of 13 ground one-on-ones, as well as seven of nine aerial duels, which was a major reason why the hosts were left frustrated for long periods.
Archie Gray can also be happy with his defensive output. The youngster won all of his aerial battles and seven of the 10 he contested on the pitch.
Gakpo makes it two
Indeed, the effort and commitment that many of the Tottenham players were showing couldn't be faulted, though they weren't really offering much in an attacking sense, with Bergvall's attempt their only one on target in the first half.
Once Cody Gakpo bent a stunning strike into the net in front of the Kop just eight minutes after the break, there was a very real sense that the game was over at that point, and over 40 per cent of the action up to the hour mark was played in Tottenham's defensive third.
Andy Robertson, on his return to Anfield, got a standing ovation and a warm round of applause from the home fans, and to his credit, the left-back completed 50% of his dribbles, found his target with 13 of his 17 passes on the night, and managed to have two touches in the Liverpool box, as did several of his colleagues.
Conor Gallagher's header with just over 20 minutes to play gave the North Londoners hope of a stirring comeback, and a raft of substitutions turned the tide Tottenham's way, albeit their efforts were generally off target or blocked once again.
Szoboszlai's screamer
That they had 17 attempts in the game but only six were on target will have disappointed De Zerbi, particularly when Liverpool scored three from their five efforts on target, saving the best until last when Dominik Szoboszlai found the top corner from 30 yards out with an opportunistic strike.
It was the first time the Reds had scored three in the competition since a February 2025 fixture... against Tottenham (4-0).
There were certainly aspects of Spurs' game that will have pleased De Zerbi and his coaching staff, but ultimately, another loss raises more question marks as to the mentality of the squad and of the Italian's way of playing more generally.
Just as with Ruben Amorim whilst at Manchester United, De Zerbi isn't for turning, and it's his way or no way.
That's all well and good when things are going well, but the problems arise when you factor in how much money the Spurs board has spent recently and what they're getting in return for their investment.