Despite only having to play away against Grimsby Town - a team playing in League Two and lacking in class, Manchester United still approached the match with great seriousness. Coach Ruben Amorim's team fielded almost the strongest squad.
Expected new signings such as Benjamin Sesko, Matheus Cunha and familiar stars Manuel Ugarte, Diogo Dalot, Harry Maguire all started.
However, Man United showed a forgettable weak face against Grimsby Town. After just 30 minutes, the "Red Devils" let Charles Vernam and Tyrell Warren of the home team score in turn.
In the second half, Amorim was forced to add Bruno Fernandes, Ryan Mbeumo and Matthijs de Ligt to turn things around. Mason Mount and Joshua Zirkzee were also brought on. Thanks to these changes, Man United played better and had a 1-2 equalizer thanks to Bryan Mbeumo in the 75th minute.
In the 88th minute, center back Maguire promptly shined with a goal to bring the match to a level 2-2, dragging Man United and Grimsby Town into a brain-weighing penalty shootout. It was thought that class and bravery would help the "Red Devils" dominate, but the scenario was completely opposite.
The two teams had to extend their shots to 13 to determine the winner, and a big surprise occurred when Grimsby Town won 12-11, turning Man United into victims of the biggest shock in the round.
Clarke Oduor was the only Grimsby Town player to miss a penalty, while Man United had two unsuccessful implementation names, Cunha and Mbeumo.
The shocking defeat against the Third Division team added to the disastrous start of the "Red Devils". In the Premier League, they have yet to taste victory after the first two rounds with 1 draw and 1 loss.