The visitors suffered a home defeat at the hands of a Belgium under-21 winger in a competition proclaimed to aid the English team.
The Checkatrade Trophy with its confused agenda and baffling purpose last night bid farewell to Pompey.
And it was to be an under-21 side which prevented Kenny Jackett’s men from progressing to the quarter-finals and taking a step closer to Wembley.
Irrespective of the strength of their Chelsea counterparts, Pompey had opportunities to take the lead during a lively opening 45 minutes.
Yet they never matched that purple period after the break.
Still, two stoppage-time goals created a dramatic finale, prompting one Blues supporter to invade the pitch at the sight of Chelsea’s winner.
Charly Musonda was the match-winner – netting twice for the visitors who had been drawn at Stamford Bridge only for the tie to be switched to Fratton Park.
The Belgium starlet netted the opener on 58 minutes and from that point Pompey offered little in attack except the occasional penalty appeal.
Then, in stoppage-time, substitute Brett Pitman swept home an unlikely equaliser and suddenly a penalty shootout was on the cards.
That was until a Pompey side reduced to 10 men following injury to Ben Close with all substitutes used, conceded a free-kick 25 yards out.
In fairness, Christian Burgess had no choice but to cynically bring down Callum Hudson-Odoi as he bore down on goal with nobody near catching.
Up stepped Musonda to finally settle matters and ensure continued progression for the Premier League club’s kids.
A lively match was watched by 3,116 – a record crowd for a Pompey game in the Checkatrade Trophy, now into its second season.
With only 113 Chelsea followers, it reflected greater interest from Blues supporters – eager to catch a glimpse of superior opposition and potential Premier League stars of the future.
The make-up of the visitors benefited their under-21 tag, unlike their 4-0 victory over MK Dons in the previous round.
Meanwhile, Connor Ronan was given his Pompey debut, operating behind lone striker Oli Hawkins.
Fellow Wolves loanee Sylvain Deslandes was named on a substitutes’ bench which included fit-again Kal Naismith.
Ronan represented the only change to the side which lost at Bristol Rovers, coming in for top-scorer Pitman.
That meant Nathan Thompson was handed the captain’s armband for the first time since joining the club in the summer.
It was Ronan who created the first goal-scoring opportunity of the fixture, rattling off a right-footed shot from outside the box on 13 minutes.
Keeper Marcin Bulka dived to his right to push the ball out and prevent the hosts taking the lead.
At the other end, Hudson-Odoi got the wrong side of Thompson and Luke McGee did well to beat his effort out at the near post.
The resulting corner delivered from the left was met with a far-post header from Musonda but it was straight at an unflustered McGee.
In the 20th minute, a patient build-up saw the ball spread to the right where Jamal Lowe fizzed in a dangerous cross which was slashed behind by Trevoh Chalobah.
The corner was supplied by Dion Donohue but Matt Clarke’s header was comfortably caught by Bulka.
Pompey continued to look threatening when Matty Kennedy’s cross from the left was met with a header by Hawkins – rising above Josh Grant. But the effort was wide.
Chelsea swiftly responded with their first substitution, Jacob Maddox replaced by Daishawn Redan on 28 minutes.
Jackett’s men were unfortunate not to break the deadlock on 32 minutes with a flurry of chances.
Firstly Hawkins’ header was palmed away by Bulka and then Lowe’s follow-up strike was blocked on the line by Kyle Scott.
The ball then fell to Hawkins once more and his left-foot half-volley was again pushed out by the busy Chelsea keeper.
It was developing into an impressive performance from the Blues, with Burgess next to contribute in the opposition penalty area, heading over Close’s free-kick from the right.
The half finished goalless, yet Pompey had been the dominant side and entered the break in good spirits.
The second-half opened with no substitutes, although worryingly Thompson had to receive treatment following a tackle with Hudson-Odoi, although was able to continue.
Moments later Clarke collected a short pass from Close and charged up the pitch past several challenges before combining with Kennedy and then squaring to Ronan inside the box.
The youngster’s shot was charged down, however, and Clarke had to retreat to his more familiar position. Pompey made a double substitution on 53 minutes with Thompson and Hawkins replaced by Pitman and Naismith.
Those changes meant Lowe dropped to right-back, with Pitman in attack and Naismith occupying the number 10 role.
Yet on 58 minutes the deadlock was broken through Chelsea’s Musonda.
Attacking down the left, Scott cut it back to the attacker who steered a shot past McGee and it the far corner of the net.
On 67 minutes, Pompey won a free-kick down the left which Ronan delivered into the box and Pitman’s backheel was blocked as it threatened to head in the direction of the net.
Close then steered the loose ball back into the box and it bounced before striking the arm of Ampadu, prompting strong appeals for a penalty, which the referee ignored.
Chelsea almost doubled their advantage on 73 minutes when Harvey St Clair’s cross from the right struck the chest of Scott inside the box and flew narrowly over the bar.
Ronan’s involvement ended on 76 minutes. He was replaced by Conor Chaplin in Pompey’s third and final substitution.
Yet the hosts had run out of ideas, while they were reduced to 10 men with Close limping off minutes later.
Then in stoppage-time, Kennedy crossed from the right and Pitman swivelled to fire home from six yards out.
The Blues now needed to hold on for penalties and Burgess was forced to bring down Hudson-Odoi as he surged through their heart, earning a booking.
Up stepped Musonda with a 25-yard free-kick which brilliantly beat McGee for a dramatic winner and it was Chelsea’s kids who progressed.