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Only one EFL club boasts worse record than Ipswich after ‘painful’ Carabao Cup exit

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Ipswich Town’s shock Carabao Cup first-round exit at the hands of League Two outfit Bromley extended two of the Tractor Boys’ unwanted runs.

Bromley went ahead at Hayes Lane through Deji Elerewere on the stroke of half-time, before the Tractor Boys hit back through Ben Johnson in the 53rd minute to equalise.

However, the home side ran out winners in the end, seeing off ex-Premier League side Ipswich 5-4 on penalties to progress to the second round of the Carabao Cup for the first time ever.

Unfortunately for Town fans, it’s not the first time in recent history they have been knocked out by lesser opposition – and Tuesday night’s loss didn’t just go on the growing list of cup disappointments.

Ipswich players losing on penalties to Bromley
Photo by Crystal Pix/MB Media/Getty Images

Ipswich boast two unwanted losing streaks after Bromley loss

Firstly, Ipswich’s defeat to Bromley means they have suffered a cup upset in every season since the 2021/22 campaign.

Most notably, Ipswich lost to non-league Maidstone United in the FA Cup fourth round in 2024, while they have also been knocked out by Bromley’s fellow League Two teams Barrow, Newport County and Colchester United in recent history.

SeasonCompetitionRoundOppositionScore
2025/26Carabao CupFirstBromley5-6 (penalties)
2024/25Carabao CupSecondAFC Wimbledon4-6 (penalties)
2023/24FA CupFourthMaidstone United2-1
2022/23Carabao CupFirstColchester United1-0
2021/22FA CupSecondBarrow2-0
2021/22Carabao CupFirstNewport County1-0

Kieran McKenna’s side have also extended their number of games without a win in a competitive fixture to ten.

The Suffolk outfit are a way off their record of 21 games without a victory that was set in 1963, but the former back-to-back promotion winners are struggling to rediscover that winning mentality that sent them from League One up to the Premier League.

Their last win came against Bournemouth in April in the Premier League, with Ipswich winning 2-1 on the day.

Preston North End had been level with them for games without a win before Tuesday night, but their victory over Barrow brought that streak to an end.

McKenna and co face fellow relegated side Southampton up next, who secured a last-minute win against Wrexham in the opening game.

While it hasn’t been an ideal start for the Blues, they’ll be hopeful that their winless run cannot go on for much longer.

Ipswich’s move for Chuba Akpom has bolstered their goal-scoring capabilities ahead of the weekend, while Jens Cajuste’s return could see him handed a second debut, improving the team on the whole.

However, Ipswich can find solace in not having the worst winless run in the 92, thanks to one other team.

Kieran McKenna looks dejected at Bromley
Photo by Crystal Pix/MB Media/Getty Images

Bristol Rovers have an even worse run without a win than Ipswich

League Two side Bristol Rovers have gone the longest time without a victory in England’s top four leagues, with a current tally of 13, thanks to their 2-0 defeat to Cambridge in the Carabao Cup on Tuesday.

Their last win came against Bolton in League One in March as they saw the Wanderers off 3-2.

This is Rovers’ longest time without victory in a competitive fixture since 2011, with The Gas’ record sitting at 20, which was set in 1980.

Rovers manager Darrell Clarke pulled no punches as he reacted to what he described as a ‘painful watch’ on Tuesday.

He said: “A painful watch. There’s no hiding from that fact. A million miles away from where we need to be. Where we need be at. I think there’s lots of circumstances in and around that as well, as to why. But listen, I can’t say no more. It’s a painful night.”

With Bristol Rovers still getting over their relegation, they will want a return to that winning feeling as soon as possible.