Manchester United have hit a new rock-bottom.
Ruben Amorim’s side fell in the second round of the 2025–26 Carabao Cup in a penalty-shootout against League Two side Grimsby Town. To make matters even worse, marquee summer signings Matheus Cunha and Bryan Mbeumo were the only players to miss from the spot.
United now have only the Premier League and FA Cup to play for this season. After finishing 15th in the top flight a season ago—the club’s worst finish since relegation in 1974—and with unconvincing performances to start the term, Amorim’s job could be under serious jeopardy.
The only reason United were even playing at this early stage is because they failed to qualify for a European competition. A second round exit from the Carabao Cup is a massive failure for a club of United’s stature. However, it’s not an unprecedented situation.
When was the Last Time Man Utd Lost in the Second Round of the Carabao Cup?
Ironically enough, United’s last defeat in the second round of the Carabao Cup came in 2014, the most recent time they played a match this early in the competition.
On Aug. 26, 2014, then League One side MK Dons dismantled Louis van Gaal’s new outfit 4–0. Benik Afobe bagged a brace, as did former Northern Ireland international and cult-hero Will Grigg. Future Tottenham Hotspur star Dele Ali also played the entire match for MK Dons.
Players such as David de Gea, Jonny Evans, Shinji Kagawa, Javier “Chicharito” Hernández, Danny Welbeck and Adnan Januzaj were on the pitch for the Red Devils.
Now, United have lost back-to-back games in the second round of the Carabao Cup.
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This article was originally published on www.si.com as When was the Last Time Man Utd Lost in the Second Round of the Carabao Cup?.
