Arsenal Football Club have quite the relationship with the League Cup.

They have not won the competition since 1992/93, losing seven finals, four of which have come this century.

There have been some shocks and scares along the way, but none bigger than Tuesday night’s incredible penalty-shootout defeat to Fleetwood Town.

It’s probably the greatest League Cup upset of all time. Fleetwood are 18th in League Two and had won only two of the nine matches they played between being drawn against the Gunners and facing them. Arsenal, meanwhile, are the reigning Premier League champions and finished runners-up in last season’s Champions League, a final they only lost on penalties.

Penalties. Bloody penalties. Arsenal won’t want another shootout any time soon. Luckily, it isn’t possible again until January, when the FA Cup third round comes around.

The FA Cup is a competition Arsenal have a rich history in, but once again f**king up in the League Cup denies Mikel Arteta and his players the chance to win the first available trophy of the season, and this defeat will especially sting having come against an out-of-form fourth-tier side.

There wasn’t any doubt going into this game. Arsenal were expected to rotate but still stroll into the last eight of the competition, and one player supporters would have been excited to see was Max Dowman.

The Carabao Cup has been Dowman’s platform to impress, with minutes hard to come by in the Premier League and Champions League, and pretty much every time he has started, he has looked bloody brilliant.

Tuesday night was the rare exception, and we were reminded that he is an actual child by his petulant kick-out that resulted in a red card in the 86th minute.

For once, things were not going his way, and a strong challenge from Harrison Neal tipped him over the edge.

An EFL loan has dubiously been mooted for the 16-year-old, and his red card should nip that in the bud. If he can’t handle challenges like that, he shouldn’t be playing in the lower leagues.

Sure, you could argue that he needs to learn how to cope with that kind of treatment and that a loan would help him do that, but the telling-off Arteta has given him is a big enough lesson. That won’t happen again, that much is for sure.

Dowman’s difficult night is secondary because Arsenal have been knocked out of a competition they expected to win, and by the club sitting 18th in League Two.

‘Champions of England, you’re having a laugh,’ sang the Fleetwood supporters against what looked like a laughable excuse for the best team in the country, who cannot be accused of taking the opposition lightly or taking the p*ss with their line-up.

They rotated, but the team was still strong. The cavalry arrived, but Fleetwood stood firm. Arsenal scored within five minutes of the second half, but Fleetwood did not crumble. For all the Gunners’ shortcomings, the Cod Army were superb and fully deserved their win.

Fleetwood were on the right end of an all-time Carabao Cup shock, but these stories are always about the team on the wrong end, and that team just happened to be Arsenal, the champions of England, 84 places higher in the football pyramid.

It’s just what happens to Arsenal in the League Cup, isn’t it? It’s a competition they are seemingly incapable of winning…