He helped the club dearest to his heart to a dramatic title win, a victory which signalled their journey back in English football and sparked a summer of glorious celebration.
The kaleidoscope of memories created from Meadow Lane’s promotion party to Fratton’s final-day title win and exultant scenes on Southsea seafront are eternal.
After 15 years at the club he loves, the ability to reflect on providing joy for those who’d suffered such pain is a reality which will endure.
And for Conor Chaplin, at the age of 21, he’s not sure that will ever be topped.
‘I was having the conversation this week,’ Chaplin said, as he reflected on a journey which saw him travel from six-year-old pup to darling of the people of Pompey.
‘After that summer starting from Notts County to coming back into pre-season, I don’t see how it’s going to get better than that.
‘I don’t see how I’m going to get a better four weeks in my life than that. I don’t know what it would take to beat it.
‘It was at a club I support and everything about it was pretty much perfect. It’s as perfect as you could get.
‘The scenes on Southsea and the final day against Cheltenham, all of that. Perfect.’
The Notts County party remains the apex for one of the club’s great academy successes of recent years.
Few have more keenly felt the struggle through two administrations which took Pompey to the brink than the Worthing lad adopted as one of our own.
‘Notts County is there straightaway,’ Chaplin smiled. ‘It’s number one definitely.
‘When I was at their ground with the fans, well, you look back and it was unbelievable.
‘There were even things like the journey back which was special. That togetherness and feeling we all had was one of the best feelings you could feel.
‘Then we got back to the stadium and the scenes were crazy.
‘You had characters in the team and every lad would’ve done anything for the other 20-odd lads. It went right the way through the team.
‘That’s unique. The more I’ve played I’ve realised that’s unique. The bond we had was special.
‘Most people involved hadn’t been there too long but I’d been there from the Premier League all the way down.
‘There hadn’t really been a high point for the club since the FA Cup win in 2008.
‘That was the first time in nine years there’d been some success, upward movement and momentum.
‘The realisation probably hit on the Sunday or Monday evening after the game, when I thought about it a bit more.
‘I was part of the squad and team who was responsible for that. That meant quite a lot to me.
‘That was because of everything which had happened in the six years before that.
‘I scored eight times in that season and there were some goals, looking back now, which got us points.
‘Barnet away sticks out but even Leyton Orient at home and Cambridge away – they were match-winning goals.
‘I’m proud to look back and feel I’ve contributed to a season where it finally started to turn for the club.’
After three years at Pompey, the day arrived when Chaplin signed his first contract as a nine-year-old, a moment marked for posterity with a picture with an early hero in Gary O’Neil.
Big noises were to later be heard over the tiny talent scoring goals for fun at youth level, paving the way for eventual first-team involvement under Andy Awford as a 17-year-old at the end of 2014.
A first goal against Morecambe followed before he came to national attention with a televised maiden Fratton Park strike against Derby.
Some special finishes and crucial interventions are Chaplin’s legacy amid 25 goals in 122 Pompey appearances, while still at a formative stage of his career.
Now a special journey is at an end following a move to Coventry but the lad stood beaming alongside O’Neil will always have that bursting pride at his Pompey bond.
‘The picture with Gary O’Neil was one my grandad sent me,’ said Chaplin after he recently shared it on social media.
‘I knew it would be somewhere because years and years ago I had it on my wall.
‘He had it still because he keeps everything. He sent it to me.
‘I was nine then. We played a game at Chelsea away, at the Cobham training ground and we had our signing afterwards.
‘You couldn’t sign until you were under-nine officially and that was the day it happened, which I’ll never forget.
‘I have so many people to thank for their help. A very big chunk of the guys who played for Portsmouth are brilliant people.
‘There’s friends I’ve got for the rest of my life I’ve grown up with.’
The outpouring of affection following news of Chaplin’s long-running move to Coventry being completed was as telling as it was heartfelt.
The suggestion he’d refused to pull on a Pompey shirt before the deal was completed was dismissed as one of the most popular players of recent years was shown the love he deserved.
What remains apparent is a lifetime association with his club has created a bond which will not be broken.
‘It’s 15 years,’ Chaplin said emotionally. ‘Fifteen years.’
‘There’s too many memories in a Pompey shirt for me. There’s not many memories I have before that time, to be honest.
‘I wrote quite a big message to supporters when the move was completed because that was genuinely how I was feeling.
‘I don’t think I need to write something to show it. I think I’ve shown it anyway.
‘But it was necessary because there’s things people don’t see and there’s people who’ve done a lot for me at Portsmouth. I couldn’t be more appreciative to those people.
‘I was just sat on my phone on my sofa writing what I thought about the club.
‘Everyone has said I never wrote it, no chance. But I genuinely did.
‘That’s the way I felt – and the way I feel about the club.’