It was supposed the perfect evening for Tottenham, but it turned into a nightmare.
Spurs were returning to the Champions League for the first time in six years and faced Monaco at the national stadium, Wembley, in front of 85,000.
But their return to Europe’s elite competition didn’t go to plan as they crumbled to a 2-1 defeat to the French side.
The match was played at Wembley due to the capacity of their White Hart Lane stadium being reduced due to redevelopment. However, Spurs will be wishing they hadn’t chosen Wembley to be their second home after their hoodoo continued.
Their loss to Monaco meant they have now been beaten on their previous five trips to Wembley - a run that stretches back to when they beat Chelsea 2-1 in the League Cup final eight years ago.
Since then they have lost to Manchester United on penalties in the 2009 League Cup, Portsmouth in the FA Cup semi-final in 2010, Chelsea twice - in the FA Cup semi-final in 2012 and the League Cup final in 2015 - and now Monaco.
While Spurs fans are no doubt bitterly disappointed over their latest defeat at Wembley, rivals fans are probably thoroughly enjoying it.
In fact, there’s no ‘probably’ about it where Piers Morgan is concerned. The celebrity Arsenal fan has taken to Twitter to mock Spurs over their recent record at Wembley.
He tweeted: “Can Spurs play at Wembley every week? #BigStadiumBigLaughs,”
Morgan’s Arsenal got their Champions League campaign off to a slightly better start with a respectable 1-1 draw away to Paris Saint-Germain.
However, for much of the clash, it seemed as though the Gunners were staring at defeat after conceding a goal after just 42 seconds and being put under heavy pressure for large periods of the match.
But Alexis Sanchez’s late equaliser managed to rescue a point, meaning Arsenal fans everywhere could rejoice 24 hours later when their north London rivals suffered a loss at the hands of Monaco.
Spurs will need to end their Wembley nightmare if they are to progress to the latter stages of the competition with two further ‘home’ matches against Bayer Leverkusen and CSKA Moscow - who drew 2-2 on Wednesday night.
Morgan will be watching closely, though, and is sure to take to Twitter is Spurs' terrible run at the home of football continues.