A heartbreaking but necessary separation, yet Portsmouth favourite's legacy remains undiminished
The popular attacker endured a difficult second Fratton Park spell with two goals in 37 appearances
Contrary to popular belief, Adrian Segecic’s shot actually struck Conor Chaplin’s thigh.
The magnificent Middlesbrough moment was dramatic enough, without crowbarring in the misconception put out by some that it was the striker’s nether regions which provided that match-winning touch.
It also represents what is likely to be Chaplin’s final scoring contribution in Pompey’s colours.
With Rich Hughes revealing to BBC Radio Solent on Monday that the Blues aren’t currently pursuing a permanent deal for the now free agent, it seems there will be no third Fratton Park spell for the hugely-likeable 29-year-old.
While last month’s 1-1 draw against Birmingham was the conclusion to the 2025-26 Championship season, it has also signalled the end of a Pompey career consisting of 159 games and 27 goals.
Desperately disappointing season-long loan
As honest as they come and a footballer devoid of ego or arrogance, Chaplin was fully aware of his failings in a desperately disappointing season-long loan with his beloved Blues.
The Ipswich man put his heart and soul into attempting to make his emotional south-coast return a success, likewise every single supporter, player and press box occupier were also desperate for him to thrive.
The brutal truth, however, is he never came close to replicating the scintillating form which made him one of the Championship’s most outstanding attacking players over a number of years.
A meagre return of two goals and three assists in 37 appearances never did his immense talent justice and, at times, it was a difficult watch. The effort, endeavour, attitude and work-rate were all emphatically present, yet it was a Pompey return which somehow still fell flat.
Fans never gave up on him
Certainly the fans retained belief in the ever-popular Chaplin, pinning their hopes that eventually, one day, soon, he would spark into life and inspire the Blues. Just give him one more game John, please.
That first assist, registered from a corner against Blackburn in December, provided much-needed hope. Then there was that long-awaited goal against West Brom in a 3-0 success in January, a moment which clearly meant the world to him.
By the time of that unorthodox winner at Middlesbrough, there were still five games remaining, perhaps this was now the time for lift off. Sadly, Chaplin found himself on the bench for the final two games.
Admittedly, there was that baffling five-game spell on the right wing at the start of his loan, yet he was still granted another 22 starts in his favoured number 10 role, plus substitute outings.
Adrian Segecic moved to accommodate
In fact, the prodigious Segecic found himself shunted to the right wing to accommodate the loanee, a switch which severely impacted on the Sydney youngster’s own performances before a late-season flurry.
Now Chaplin has departed, you can imagine that the 22-year-old will be offered more opportunities in a 10 role which appears to be a far more natural fit - and rightly so.
Of course, considering the deep affection many fans continue to hold for Chaplin, it was entirely natural that some called for a return once more following his release by Ipswich last month.
It’s reassuring that strong connection still remains, his immense Pompey legacy doesn’t deserve to be tainted by that disappointing second stint.
We’ll always have the League Two title, his first career goal at Morecambe, that wondrous Wycombe goal, the rocket of an equaliser at Barnet, sprinting the length of the pitch to celebrate at MK Dons, the leveller in the first bitter reunion with Paul Cook at Wigan.
Plus that iconic moment at Middlesbrough, when his thigh diverted Segecic’s volley past Sol Brynn to register a first timely win in nine matches to kick-start another Championship relegation escape.
Conor Chaplin’s place in Fratton folklore is undiminished.
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