Max Dowman entered the record books on Tuesday after receiving a red card during a match against Fleetwood.
At 16 years old, the teenager became the youngest player ever dismissed in both the Carabao Cup and professional English football overall.
While players naturally try to avoid such milestones, Arsenal has seen this happen several times before.
Among the eight youngest players to receive a straight red card in a major English tournament, four belonged to Arsenal.
Myles Lewis-Skelly held the previous club distinction before Dowman, coming close to the overall record when referee Michael Oliver dismissed him against Wolves in January 2025.
At 18 years and 121 days old, the versatile player received his marching orders for a foul on Matt Doherty.
Wayne Rooney remains the only player younger than Lewis-Skelly to get a straight red card, having been dismissed for Everton against Birmingham in 2002 when he was 17 years and 63 days old.
Lewis-Skelly earned another dismissal less than a month later against West Ham after pulling down Mohammed Kudus.
Cesc Fabregas, now managing Como, was an 18-year-old breaking into Arsene Wenger's Arsenal squad back in 2006.
He pushed Tim Cahill in the face during stoppage time against Everton, earning a red card at 18 years and 262 days old to rank as the seventh youngest player sent off.
Another creative Arsenal midfielder, Jack Wilshere, claimed the eighth spot on the list.
He was just 26 days older than Fabregas when he received a red card for tackling Birmingham player Nikola Zigic near the end of a 2010/11 Premier League fixture.
Dowman shares this unfortunate trend with numerous other football stars who faced early dismissals.
Wayne Rooney held the youngest record prior to Dowman, while Michael Owen stands as the third youngest player sent off in English football following two yellow cards for Liverpool against Manchester United in 1998 at 18 years and 117 days old.
Shea Lacey of Manchester United became the youngest player dismissed in the FA Cup during the 2025/26 season at 18 years and 272 days old after receiving two quick yellow cards.
Several international stars also saw red early in their careers, including Lionel Messi during his Argentina debut against Hungary as an 18-year-old after elbowing a defender.
Barcelona defender Pau Cubarsi was sent off against Benfica in March 2025 at 18 years and 42 days old.
Cristiano Ronaldo received a one-match ban at age 15 while playing for Sporting Lisbon following an argument with his coach.
Dowman reportedly ignored public criticism from Mikel Arteta as he left the pitch on Tuesday.
