Pompey were left to rue a handful of wasted first-half chances as a side packed with Academy youngsters tumbled out of the Johnstone’s Paint Trophy in a 2-0 defeat at Exeter City.
A penalty early in the second-half from Ryan Harley and Alex Nicholls’ 72nd-minute clincher settled the tie but there were plenty of positive glimpses of players who should go on to become first-team regulars in the coming years as Paul Cook opted to go with youth.
It was made crystal clear before the game that Cook was planning to rotate the squad.
Perhaps we all underestimated exactly how much he was going to do it.
Three 17-year-olds from the Academy were in the starting line-up in Adam May – a first-team veteran from last season – alongside debutants Brandon Joseph-Buadi and Calvin Davies.
And there were four more teenagers from Mikey Harris’ ranks among the substitutes for good measure
There was also a debut for Adam Barton, who had finally shaken off a groin injury after his summer move from Coventry City.
Ben Tollitt was also handed a first start after two substitute appearances in the Capital One Cup.
The 29-year-old Paul Jones in goal was the elder statesman as he returned to his former club.
Ben Close skippered the side, while up front Adam McGurk – at the ripe old age of 26 – was the old head on the pitch.
Ahead of kick-off, there was the usual smattering of the old jokes of suggesting it was past some of their bedtimes but the 515 travelling fans certainly showed their appreciation at the final whistle.
If there were a few nerves jangling beforehand, they didn’t show and Pompey should have been ahead with just 13 seconds on the clock.
A diagonal ball looking for McGurk should have been tidied up by the Exeter defence without too much fuss but they somehow missed it to spring the former Burton Albion man clean through on goal.
He should have buried it but his attempt to bend it into the bottom corner lacked the necessary disguise and the goalkeeper palmed the ball to safety with relative ease.
If that early chance sparked hopes of Pompey’s youngsters running riot, the reality of the game was rather different as Exeter dominated the opening quarter of the contest, even though they failed to create anything as clear-cut as McGurk’s chance.
The lively David Wheeler headed a cross from former Pompey loanee Lee Holmes on to the roof of Jones’ net.
The right-back Davies, reminiscent of a younger John Beresford on the opposite flank with his hitched up shorts and gutsy character, charged down Danny Butterfield’s drive and gave a performance that suggested he would be more than capable of stepping up to fill in for namesake Ben as a League Two deputy.
Wheeler had the ball in the net soon afterwards, only for the celebrations to be stopped in their tracks after he’d shoved Adam Webster in the back before his deft lob dropped into the net.
Even though Exeter had the edge in terms of territory and looked the more threatening going forward, Pompey certainly had their moments and created three more excellent opportunities before the interval.
Perhaps growing into the game and increasing in confidence, the Blues began to find their rhythm with their passing as Close and May started to gain more of a foothold in midfield.
A lovely piece of build-up play on the half-hour mark culminated in May sending Chaplin through but his angled effort was kept out by the keeper’s legs.
And with Pompey definitely on top as half-time approached, the increasingly influential Chaplin slid Tollitt through.
But he sliced his effort high and wide when he should have done better.
Chaplin took the responsibility himself in the moments before the break after Davies was chopped down on a break forward.
Although the angle for the free-kick didn’t look too favourable, the young talent still found enough whip on his set-piece to rattle Bobby Olejnik’s crossbar.
It was the last act of an open and entertaining half but there was just the hint that Pompey may live to regret those missed opportunities.
That became even more apparent just nine minutes after the restart as Exeter grabbed the lead.
There appeared to be little danger in a Grecians attack until Tom McCready made a burst through the inside right channel.
But with Joseph-Buadi seemingly caught napping, the youngster hauled down the City man just inside the area and referee Lee Swabey had no hesitation in pointing to the spot.
Harley gave Jones no chance as he slammed home the penalty and, even at that early stage in the half, it had the feel of a strike to settle a tie.
After their first-half efforts going forward, Pompey were showing far less in attack with Exeter taking charge.
Only Chaplin and the odd fleeting moment from Tollitt looked likely to deliver an opening to McGurk, who never got another sight of goal before he was substituted 13 minutes from time.
But by that stage, Pompey were 2-0 down and pretty much out of the competition at the first hurdle.
The second goal effectively killed off any hopes of an extended run for the youngsters and it looked a soft one to concede from Jones’ point of view.
It seemed hard to see how Nicholls could find the net from around 25 yards out and on a tight angle but his angled shot somehow deceived Jones as it found the far corner.
It certainly didn’t look like it had any real pace on it to cause too many problems but it was enough to give the home side a two-goal advantage.
It confirmed what we all thought might happen – a plucky effort from plenty of young players with lots of potential but ultimately a defeat in the first round of the Johnstone’s Paint Trophy.
There was still time for two more debuts in the shape of Kal Naismith and Christian Oxlade-Chamberlain – younger brother of England star Alex – but any hopes of a trip to Wembley in this competition are over.
Cook will maintain his priorities lie elsewhere this season and most Blues fans will agree with that philosophy.
But he will be looking for instant evidence this weekend at home to Accrington.