Wayne Burnett took his Spurs U23's down the road to the Emirates to take on Freddie Ljungberg's Arsenal.
Unfortunately for Spurs, they left the red half of North London with nothing as an early Joe Willock goal and a goal from Tyreece John-Jules midway through the second half gave Arsenal all three points.
Spurs did pull a late goal back through Jaden Brown but it wasn't enough. Here are five things we learned about Burnett's side.
Troy Parrott: Could he be the next Kane or Keane?
The young Irish forward caught everyone's eye at the recent U17 European Championships held in England. Particular attention was paid to a beauty of a free kick he scored against Bosnia. One that a certain Kieran Trippier would have been proud of.
Parrott obviously impressed Burnett enough to convince the board to extend the Irishman's contract back in May, but is it the case of people boarding the hype train, before the youngster has really proven himself at senior level?
There have been calls, similar to those last year for Reo Griffiths, that Parrott should be promoted to become Harry Kane's understudy. This has been somewhat of poison chalice as all three strikers who have played this role, have either disappeared; Vincent Janssen, or saw their careers damaged greatly; Fernando Llorente and Roberto Soldado.
The other comparison that has been banded about is to fellow countryman and Spurs legend Robbie Keane.
On the evidence of their defeat to Arsenal, it is way too early to even contemplate promoting the youngster. Parrott found chances at a premium, as Arsenal cut off his service completely and he also lost his temper late on in the game and got himself sent off after a bust-up on the pitch.
Let's see how he performs upon his return, especially in the upcoming Checktrade Trophy, which is a whole lot more physical than PL2.
Should Danny Rose be looking over his shoulder?
One player who did truly impress on the night was left back, Jaden Brown.
Brown kept Arsenal attacks to a minimum down his side and like the senior players, Brown attempted to push on forward when he could and was rewarded right at the death as he was able to find a way into the Arsenal box and score to make it a tense last few minutes.
After the moderate success Kyle Walker-Peters has found when he has been thrust into the first team, could Brown be the next youth player to be given a chance? Given all the uncertainty surrounding Rose throughout the summer Mauricio Pochettino could be prepared to give Brown the chance to make his mark in the senior squad, maybe in cup competitions.
Oliver Skipp the linchpin
Having just signed a brand new contract, Oliver Skipp repaid the faith somewhat with a very assured performance at the Emirates.
Skipp played the role similar to that of what Eric Dier does in the senior squad, which is to sit in front of the defence and link the two together.
Skipp did, however, find it difficult to create much going forward. As previously mentioned Arsenal did a very good job of cutting off the service to the forwards. Skipp does look like a tidy little player and could be another one of the midfield gems coming out of Hotspur Way.
Spurs found it hard to break Arsenal down
As hinted at in previous parts, Spurs found it quite hard to break the Arsenal defence down and chances were really at a premium for Parrott and Shayon Harrison.
As the season goes on, Spurs could be in serious trouble near the foot of the PL2 table.
The main problem is that the best of Spurs' youth seems to be shipped off on loan in the search for first-team football or kept on the bench of the first team.
This may sound like a good thing but what it does mean is that there is a lack of team cohesion due to the fact that the same players are not always together.
If Spurs held onto the likes of Marcus Edwards and Conor Ogilvie then the youth squad might perform better. However, you just have to look at the youth setup at Chelsea, they always seem to perform well at this level but it's rare to see any of those players in the first team.
The Pochettino brand of football is alive and well
One major positive to take from the game is the style of play Spurs implemented.
Burnett has got the U23 side playing a quick passing game and they tried to keep as much of the ball as they could. Pochettino has obviously made it a priority to get this style of football played at all levels throughout the club.
The only problem that Burnett has run into is the lack of team cohesion, and a lack of older heads in there to really dictate the game.
Having players like Edwards, Ogilvie and Anthony Georgiou who have been in an around the club for a few years can really help the others players' development.