Anfield has never been a happy hunting ground for Tottenham Hotspur, who managed to add another disappointing chapter to their history there on Tuesday night with a 3-1 Carabao Cup defeat to Liverpool. Here are our three biggest losers and our three tentative winners from the encounter. Tuesday 15th September League Cup LiverpoolLiverpool3|1TottenhamTottenhamMarcos Senesi struggled with the pace of the game In his first cameo since Spurs’ opening day defeat to Brentford, Marcos Senesi was given the chance to at least put in a challenge or an argument for more consistent involvement in Premier League squads. His Liverpool performance probably will not have Roberto De Zerbi convinced.The Argentine showed how far he is from full match sharpness when he struggled under pressure from Liverpool’s press and put his team in a few uncomfortable situations, such as conceding a high-quality chance to Liverpool’s Koumas. His passing from deep proved useful a few times, especially when he was able to access the final third directly, but defensively it was a below-average performance from the centre-back.Photo by Michael Regan/Getty ImagesMathys Tel continues to baffle Tottenham fansDespite being arguably Spurs’ best player of the pre-season, yesterday’s game at Anfield proved to be yet another poor senior appearance for the French player. Despite playing almost the full 90 minutes, only coming off in the 85th to make way for Dominic Solanke, any positive impact Mathys Tel had on the team was difficult to nail down.Playing off the left, Tel’s appearance carried all the hallmarks we’ve seen from him many times in a Spurs shirt. Mathys Tel got on the ball in some dangerous situations and always looked busy, but his end product again remained seriously lacking.Currently, Mathys Tel’s game is suffering heavily from a kind of one-dimensionality, possibly due to coaching, manager instructions or a lack of experience. Tel consistently shows the intent to beat his man 1v1, either in a dribble or a foot race, but if his fullback grows smart to his dribbles or is quicker than him, the winger suddenly looks completely impotent and bereft of ideas.With all the raw qualities that Mathys Tel has, particularly in his ball striking, there is a lot of hope for Tel’s development, especially if he manages to add different kinds of goal threat to his toolbox. But that still looks far off from materialising.Roberto De Zerbi makes his own bed againIn a team that was all shades of poor on the night, picking De Zerbi as our final loser of the fixture may be surprising, but the Italian manager made a series of strange calls in the lead-up to and during the match.Although selecting a rotated lineup is almost a necessity with a squad the size of Tottenham’s, making seven changes from their Premier League matchday was always going to impact the team’s already poor cohesion.The Anfield game is also yet another in a series of team selections with an almost incompatible midfield selection given De Zerbi’s ideal game model. Conor Gallagher, Lucas Bergvall and Rodrigo Bentancur were almost completely ineffective in sustainably building attacks through the middle of the pitch due to their combined lack of creativity and technical ability.But what about the three winners from the game?Credit: @reclusemedia / InstagramDestiny Udogie’s presence on the left is transformative to TottenhamAfter missing out on an involvement against Everton with a knock, Udogie once again showed his undeniable value to the team in his start against Liverpool.The left back was crucial in creating two of Spurs’ clearest-cut chances of the game, and if not for Spurs’ woeful finishing, he would have ended the game with two assists.Udogie’s defensive abilities proved more than a match for Rio Ngumoha, while the threat of his underlapping runs consistently created tensions in Liverpool’s press and defensive structure.The only thing that keeps Udogie from realising his potential as a world-class fullback is his patchy injury record, but if Tottenham’s revamped medical team succeeds in the monumental task of keeping the Italian fullback fit over the course of the season, there is no reason for Udogie not to have his best season yet.Mateus Fernandes showed why he must start in the pivot roleMateus Fernandes’ substitution for Rodrigo Bentancur in the 57th minute was one of the two biggest turning points of the game for Spurs (the other one being the appearance of James Maddison).Until the Carabao Cup game, Fernandes was confined to playing the no. 10, a role he was desperately unsuited for.Receiving his first minutes as part of a double pivot and excelling in that role hopefully means we can expect Mateus Fernandes to start as the midfield anchor in Tottenham’s Premier League fixture against Aston Villa on the weekend.The introduction of Fernandes’ technical ability and creativity with his passing completely changed the dynamic of the fixture against Liverpool. With Spurs’ backline gaining access to a consistent out-ball in Fernandes, a player confident enough to receive a pass in tight spaces, turn with the ball and play forward, the team were suddenly able to construct attacks, maintain possession and play out from the back, all the while forcing Liverpool’s press into a less aggressive approach.In his 30-minute cameo, he managed to complete more passes into the final third (5) than any Spurs player besides Senesi (9) and while his dead-ball delivery was a known quantity too, the assist for Conor Gallagher’s header is a nice cherry on top of an already impressive performance.Tottenham need James Maddison back in the starting XIIf one thing remains true from the end of last season to now, it’s that Spurs are always a better team with James Maddison in it and they suffer every day he spends on the sidelines.Introduced on the 75th minute for Conor Gallagher, he spearheaded a significantly more balanced and functional midfield triangle with Lucas Bergvall and Mateus Fernandes.With James Maddison and Mateus Fernandes both on the pitch, Spurs suddenly found themselves with multiple solutions for central ball progression, which again completely changed the tactical makeup of the game. Liverpool, now more afraid of leaving gaps behind their press, were forced back, giving Spurs time and space on the ball and more consistent access to their final third.Maddison’s outside-of-the-foot pass which played in Omar Marmoush is perhaps the most memorable moment and shows how desperately Spurs have missed a player of his creativity, talent and technical ability since his ACL injury in 2025.In his 20-minute cameo, for the first time this season Spurs truly looked like a Roberto De Zerbi side, hopefully giving the manager a blueprint to follow. READ MORE: De Zerbi insists he must take blame for Martin Dubravka mistake in Tottenham defeatThe post Three winners and three losers as Tottenham taste Carabao Cup defeat at Anfield appeared first on Spurs Web.