Tottenham Hotspur succumbed to a defeat on penalties after a 0-0 bore draw away at Colchester United, continuing their horrific away form in 2019 and getting knocked out of the Carabao Cup in the process.
Mauricio Pochettino named a heavily rotated side which saw young prospects Oliver Skipp, Japhet Tanganga and Troy Parrott being given a chance alongside experienced players like Eric Dier, Victor Wanyama and the hero of Amsterdam, Lucas Moura.
However, Spurs failed to put the ball in the back of the net or even trouble Dean Gerken in goal for Colchester as Parrott struggled to receive service and Dele Alli and Lucas Moura failed to create chances.
In the shootout, substitute Christian Eriksen's penalty was saved before Paulo Gazzaniga saved Jevani Brown's attempted panenka - only for Lucas to have his attempt ping back off the crossbar and Colchester to win on penalties.
Story of the match
Spurs struggled the entire game to gain any momentum and potshots from Alli and Lucas provided evidence of this.
The best chance of the first half came when Kyle Walker-Peters, who was given the freedom of the right flank, got to the byline and pulled back to the middle of the box for Alli who dragged his attempt wide.
Parrott struggled to influence the game as he so often has at youth level and did in pre-season this summer, but the young Irishman did show great skill at the end of the first half to drive his team forward after a very clever turn out wide on the halfway line before spreading play out wide.
The youngster was presented an opportunity which he blazed over the bar, and another in the second half which looked destined for the far corner but was blocked by a Colchester defender.
Colchester themselves did not have a real sniff of goal in the 90 minutes, but their defence was resilient enough to take the game to penalties.
Eriksen continued his poor penalty record for Tottenham by having his low penalty saved by Gerken.
Gazzaniga then punched away a cheeky panenka attempt from Brown who was furious with himself afterwards - and quite rightly so, until his blushes were spared.
The usually reliable and heavily experienced Lucas struck his penalty high and into the crossbar, leaving Tom Lapslie with the chance to send Colchester into the League Cup 4th Round draw - which he then in turn did.
Takeaways from the match
Woeful away form
Tottenham seem woeful still away from home - this needs to change if they are genuinely going to challenge for a top-four spot - let alone for the title which looks pretty much out of reach for the North London side now.
Pochettino's side have not won in the Premier League away from home since beating Fulham on the 20th January 2019 - a truly dire statistic.
Failure to provide service to Parrott
The 17-year-old Irish striker was given an opportunity upfront for the first time in a competitive fixture by Pochettino, but ultimately his teammates failed to create any real clear chances for him.
Parrott had a few shots in the game at best and was often isolated in the middle or driven wide when Lucas was trying to create something in the centre of the pitch.
It was a showing of promise however from the young prospect, labelled as the next Robbie Keane, as he showed great work rate and off the ball movement - which was failed to be capitalised on by the creative players around him in Alli and Lucas.
Woeful team selection
One thing on many Spurs fans minds was the team selection - and one area in particular which was the three central midfield spots.
Three defensive-minded midfielders, Eric Dier, Victor Wanyama and Oliver Skipp all started against the League Two side - a shocking selection from Pochettino given that Colchester were always going to have their entire team behind the ball most of the game.
Only Pochettino knows what he was thinking and wanting from his players, but one thing is for certain - Spurs lacked creativity and forward-thinking from deep.