The underwhelming free transfer from Gillingham who blossomed into a priceless Portsmouth favourite
The former Spurs Academy youngster has made 196 appearances and scored 13 times since joining in August 2021
Danny Cowley’s first transfer window as permanent Pompey head coach was largely focused on the loan market and freebies, having initiated something of a clear-out of club stalwarts.
Squad numbers had significantly depleted in the summer of 2021 following departures of the likes of Tom Naylor, Andy Cannon, Craig MacGillivray, Ben Close, Jack Whatmough and Ryan Williams.
Of the new signings, Ryan Tunnicliffe had won the FA Youth Cup at Manchester United alongside Paul Pogba and Jesse Lingard, while Manchester City and Republic of Ireland international goalkeeper Gavin Bazunu joined on loan.
Kieron Freeman was a Wales international who had featured for Sheffield United in the Premier League, while Shaun Williams had spent six seasons as a Millwall regular in the Championship.
Then there was a free transfer from Gillingham, recruited five days before the start of the 2021-22 League One season.
Approaching five years later, Connor Ogilvie is Pompey’s longest-serving player and, on Wednesday, signed a new two-year contract.
‘He’s one of those you don’t have to worry about, proper low maintenance’
Recalling the defender’s arrival, former Pompey first-team coach Simon Bassey told The News in 2025: ‘He was one I recommended. We did a lot of data stuff at Wimbledon and he always comes good on the data.
‘He’s not one that looks great on the eye, certainly when he had his old haircut, but he is steady, reliable, honest, comes up with a goal and defends his back post.
‘I looked at the data and it said he was good. We all agreed he would be a good, reliable, steady player for us, so we signed him. And he has proven that.
‘There were others in for him, he was coming out of Gillingham on a free, so there were other options. But at that level, Pompey should really be a club people go for.
‘Once we met Connor, he was fine to move down with his girlfriend and we never had a minute’s problem. He’s one of those you don’t have to worry about, proper low maintenance, yet a brilliant kid, quite funny in his own way, a bit dry, although quiet.
‘You don't have to worry about him, he knows what he is, he’s worked it out. Good players adapt and find the solutions. You don’t have to tell him too much, he does it. He doesn’t need getting up for anything, he turns up every day ready to work.’
Portsmouth debut as a central midfielder
Although Ogilvie has since amassed 196 appearances and 13 goals, curiously his Pompey debut arrived in the centre of midfield.
Heading to Fleetwood in August 2021 on the opening day of the season, fellow newcomer Williams pulled up during the on-pitch warm-up, prompting Cowley to initiate last-minute changes to his starting XI.
Having been earmarked for bench duty, Ogilvie was promoted to midfield - a position he had never previously played in his career - and subsequently completed the full 90 minutes in the unfamiliar role.
As it turned out, left-back Lee Brown was the match winner in a 1-0 success, representing an encouraging start to the season for Cowley’s men, who ended the first month in fifth.
Ogilvie soon settled into a centre-half role alongside Sean Raggett, although, on occasions, he featured in a back three when Blackburn loanee Hayden Carter joined the pair in defence.
Switch to left-back
Incidentally, Brown departed for AFC Wimbledon midway through that season in January 2022, with Denver Hume having been recruited from Sunderland as his replacement at left-back.
Cowley finally turned to Ogilvie in March 2022 for the visit of Accrington Stanley to Fratton Park. Pompey won 4-0 - and he has largely remained first-choice left-back ever since.
From an under-the-radar free transfer signing from Gillingham to a regular performer in the Championship, it has been quite the journey over the last five years. And it hasn’t ended.
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