It was a heart-destroying night for everyone affiliated with Tottenham Hotspur on Tuesday evening. Bayern Munich drubbed the Lilywhites 7-2.
Former Arsenal winger Serge Gnabry scored four at the Tottenham Hotspur Stadium - and then rubbed salt into the wounds of Spurs fans by tweeting "North London is Red."
Spurs made history again yesterday just over four months after qualifying for a Champions League Final for the first time.
However, contrary to the scenes in May, Spurs made records for all the wrong reasons as they became the first English side since 1995 to concede seven goals in one game - ironically the last side to achieve that feat was also Spurs against Cologne in the Intertoto Cup.
The result sees Spurs' torrid run of form resume and questions over Mauricio Pochettino's future continues to be asked - but what is going on at Spurs?
Christian Eriksen, Jan Vertonghen and Toby Alderweireld all look set for the exit door at Spurs with less than a year left on all of their respective contracts.
The media have been driving the speculation surrounding each player's future which is believed to have caused tension in the dressing room and a suggestion that the players are too unsettled to give 100% to the club.
Pochettino himself has commented on the dressing room and its unsettled state in recent weeks. He's even labelled it as the reason for a few poor results.
Eriksen is being linked with a January move to Real Madrid while Alderweireld has been linked with numerous clubs in Europe such as Manchester United, Roma and Paris Saint Germain in the past.
Vertonghen, however, has suggested he may be able to still play for Spurs for another two years and it appears likely he may sign a contract extension.
Danny Rose, Victor Wanyama, Serge Aurier and Eric Dier were all reportedly made available for transfer in the summer too - but none were moved on.
The unsettled dressing room is perhaps the biggest problem at Spurs right now. The side looks far from the team it did a couple of years ago. Back then, it seemed to be so together and the players enjoyed their football and playing for the club.
Where is Pochettino's head at?
It's no secret that Pochettino has been unhappy with how things are run at Tottenham. It was evident during pre-season. He referred to himself as a coach because he doesn't believe he has control over certain decisions that a manager typically would.
Speculation has been rife over the Argentine's future with Real Madrid and Manchester United supposedly lining him up - but there is a huge possibility that he could become the Argentina national side's manager in the future.
Spurs themselves have been linked with different managers in recent weeks too, with names such as Brendan Rodgers, Eddie Howe and even Gareth Southgate being banded about.
Massimiliano Allegri was spotted in the stands to watch Spurs against Bayern which has also fuelled speculation that he may be about to take the reigns at the North London club.
The question is, though, if Pochettino leaves, will he be sacked or will he walk?
The last time Spurs were lining up consistently with a defensive midfielder in the side was in the 2016-17 season where the midfield partnership of Victor Wanyama and Mousa Dembele was actually considered one of the best in Europe at the time.
Another factor that contributed to Tottenham's displays was their high flying full-backs Danny Rose and Kyle Walker - with the latter since moved on to Manchester City and Rose's form dipping since then.
It seems like a long time since that season, where Spurs conceded just 26 goals all season in the Premier League - 8 goals more than what Spurs have already conceded this season in all competitions.
One thing's for sure, Spurs need to sort out their defensive issues and if history was to direct Pochettino towards a solution, utilising a defensive midfielder and strengthening the full-back positions should be a priority.
What can be fixed?
Unfortunately for Spurs fans, the issues surrounding players like Alderweireld's and Eriksen's futures need to be resolved as soon as possible and it seems near-certain that the only option for Pochettino is to sell the players in January.
A mass clear-out of players who are not playing for the badge anymore is needed for Spurs to begin recreating a settled dressing room and environment.
Paulo Dybala is a name that is consistently being linked with Spurs, as the Juventus forward is being frozen out by his club.
The Argentina international almost completed a move to Spurs on deadline day in August - but issues with the player's image rights scuppered the deal.
Pochettino is believed to be interested in bringing his compatriot to North London - however, it is unclear whether the player himself will still be willing to make the move if the current Spurs boss leaves the helm.
Spurs look set for a busy January as it's rebuild time - but will it be Pochettino reshaping the side and fixing the underlying issues or will it be another name in control for the North London side?