Tottenham's difficult start to the season continued as Liverpool's second-string side sent Spurs crashing out of the Carabao Cup, while Arsenal, Fulham, Brentford and Peterborough United all booked their places in round four.
Liverpool 3-1 Tottenham Hotspur
Goals from Alexis Mac Allister, Cody Gakpo and Dominik Szoboszlai saw Andoni Iraola's Liverpool progress at Tottenham's expense, though Roberto de Zerbi's side did at least end a run of four league games without scoring against Premier League opposition.
Both managers made wholesale changes. Iraola shuffled his pack by 10 from Saturday's goalless draw with Fulham, with only Ronald Araujo retaining his place and Joe Gomez captaining the side on his first appearance of the campaign. De Zerbi made eight alterations from Spurs' stalemate with Everton, handing Andy Robertson a place on the bench for his first return to Anfield since his summer departure.
Giorgi Mamardashvili denied Spurs an early opener with a fine save from Lucas Bergvall before Mac Allister broke the deadlock on 21 minutes, side-footing home from the edge of the box. Mohammed Kudus should have levelled shortly after the half-hour but blazed over from close range, and Liverpool made the miss count after the break as Gakpo finished off a slick move set up by Mac Allister.
Robertson's introduction was greeted with a standing ovation from the Anfield crowd, and Spurs found a route back into the game when Conor Gallagher turned home Mateus Fernandes' corner in the 69th minute - their first goal against Premier League opposition this season. Mamardashvili produced another crucial stop to deny Omar Marmoush before Szoboszlai settled matters in injury time, chesting the ball down and rifling a long-range effort into the net.
Spurs have now lost three of their six games in all competitions this season, with their only win coming against Charlton in the previous round of the competition.
Ipswich Town 2-4 Arsenal
Max Dowman scored twice as Arsenal eased into round four with victory at Ipswich Town.
The 16-year-old opened the scoring in the seventh minute with a fine solo effort, winning the ball in midfield before combining with Eberechi Eze and finishing well. Noni Madueke doubled the lead from Mikel Merino's flicked pass, and Dowman added his second after the break with a composed finish following Martin Zubimendi's through ball. Merino completed the scoring off the inside of the post.
Ipswich responded through Anis Mehmeti, finishing from Jack Clarke's pass, and Chuba Akpom, who turned and finished tidily, but it proved too little too late for the hosts.
Both sides made heavily changed line-ups, with a combined 19 alterations from their weekend fixtures - Arsenal also handing a first start of the season to centre-back Marli Salmon, 17. Arsenal, who remain unbeaten this season, will learn their fourth-round opponents in Wednesday's draw.
West Ham United 2-3 Fulham
Substitute Oscar Bobb struck his first goal for Fulham to send Alvaro Arbeloa's side through at the expense of West Ham in an eventful tie at the London Stadium.
Before kick-off, West Ham fans paid tribute to former goalkeeper Ludek Miklosko, who made almost 400 appearances for the club between 1990 and 1998 and passed away recently at the age of 64.
Fulham made the brighter start, Rodrigo Muniz heading in from Cesar Palacios' cross after good work from Antonee Robinson. Konstantinos Mavropanos set up Morato to level within three minutes, but Fulham regained the lead when Joachim Andersen's pass sent Palacios clear to lift the ball over the goalkeeper for his second goal in successive games. West Ham drew level again right on half-time as Kyle Walker-Peters' cross was parried into the path of Pablo, who forced the ball in from a tight angle.
Bobb, introduced in the 69th minute, proved the difference eight minutes later with his first goal since last summer's Fifa Club World Cup. West Ham pushed for an equaliser late on - Taty Castellanos seeing an effort cleared off the line by Timothy Castagne - but could not find a way through, their six-match unbeaten run coming to an end.
Arbeloa made nine changes from the side that drew at Liverpool on Saturday. West Ham return to Sky Bet Championship action against Millwall on Saturday, while Fulham host Manchester United in the Premier League on Sunday.
Reading 1-2 Brentford
Brentford secured a hard-fought win at League One's Reading to book their spot in round four.
Callum Wilson opened the scoring inside three minutes, finishing calmly after Dango Ouattara's pass caught out the home defence, and Ouattara turned provider again early in the second half to send Fabio Carvalho through for Brentford's second - a first goal for Carvalho since rupturing his anterior cruciate ligament in November 2025.
Reading pushed for a way back into the tie and had strong penalty appeals turned down before Paudie O'Connor headed in from a set-piece in the 71st minute to reduce the arrears. The League One side also had an overhead-kick effort ruled out for a high boot in the box, and saw a stoppage-time header from Jannik Schuster disallowed for a foul, as Brentford held on for victory.
Brentford, quarter-finalists in each of the last two seasons, will discover their next opponents in Wednesday's draw.
Peterborough United 3-3 Barnsley (Peterborough win 7-6 on penalties)
Peterborough United reached the Carabao Cup fourth round for the first time since 2009, edging out Barnsley 7-6 on penalties after a dramatic 3-3 draw between the two League One sides.
Barnsley led inside a minute when Cameron McGeehan headed in after Peterborough goalkeeper Alex Bass was charged down. Peterborough responded through Harry Leonard, who prodded home after Kieran Flavell could only push out Lucca Mendonca's cross, before Danny Ormerod headed in Harley Mills' free-kick to complete the turnaround. Reyes Cleary levelled for Barnsley shortly before the break with a well-placed finish from the left.
Cleary put the visitors back in front with 16 minutes remaining, but Ormerod's second header of the night, from another Mills cross, forced a shootout with two minutes of normal time left. Peterborough held their nerve from the spot, Bass saving Luke Alker's effort before Harrison Jones converted the winning penalty.