Newcastle United’s Carabao Cup-winning captain Bruno Guimaraes missed a crucial penalty in Arsenal’s shootout defeat to League Two side Fleetwood Town on Tuesday night.

The Brazilian was a late substitute in the match with the score at 1-1 after Aaron Loupalo-Bi’s first-half opener for Fleetwood was cancelled out by Viktor Gyokeres’ effort in the second half. Max Dowman was sent off in the closing stages for Arsenal before the match went to penalties at Highbury (not that one).

After seven perfect spot kicks, Guimaraes stepped up to take his penalty but saw his effort saved by Fleetwood goalkeeper Jay Lynch. It proved to be the only unsuccessful penalty in the shootout as Conor Haughey then converted to send Fleetwood through to the quarter-finals as 5-3 winners on penalties.

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Along with a shock exit for Arsenal and giant-killing for Fleetwood, it marked the first time Guimaraes had failed to reach at least the quarter-finals of the Carabao Cup.

In his four full seasons at Newcastle prior to his £75million move to Arsenal in the summer, Guimaraes reached the final in 2022/23, quarter-final in 2023/24, won the competition in 2024/25 and reached the semi-final last season.

Bruno Guimaraes’ penalty woes continue

In addition to being knocked out of the Carabao Cup at a surprisingly early stage by his standards, Tuesday night’s penalty miss also continued a concerning trend for the midfielder.

The penalty was Guimaraes’ first since his high-profile penalty miss in the World Cup last-16 defeat to Norway in the summer. And has once again played a decisive role in denying his side a quarter-final spot.

The 28-year-old has also missed three of his last four penalties for club and country having also missed in Newcastle’s FA Cup shootout win over AFC Bournemouth back in January before converting from the spot a few weeks later in the Premier League defeat to Brentford.

The Brazilian also missed a penalty for Newcastle in the shootout win over Crystal Palace in the Carabao Cup back in 2022.

Now Newcastle will be hoping to avoid being knocked out before the quarter-final stage themselves as they face Everton on Thursday night.