RESOLVING THE LEDGER
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Conor Masterson in action for Gillingham against Kion Etete of Cheltenham Town in April 2022 / | NurPhoto via Getty Images
Reading made their sixth signing of the summer this week, and he’s actually already played twice for the first team now. Conor Masterson appeared against Charlton Athletic in the Royals’ final pre-season friendly as a triallist, and made his competitive debut on Tuesday evening at Stevenage, a matter of hours after joining, doing pretty well too .
Still, we wanted to find out some more about his time at former club Gillingham, where he’d been for the last few years, across multiple spells. Thanks very much indeed to The View From The Medway Fancast for a detailed, in-depth take on Masterson’s spell with the Gills. You can find them on Twitter @TVFTM and their website right here .
How would you sum up his time at Gillingham?
He became a very popular and important player at Priestfield. Masterson had three spells with us: two on loan before making the move permanent in summer 2023. By June 2025 he had made 112 appearances for the club, scoring nine goals.
His peak was undoubtedly 2023/24. He played 48 times in all competitions, scored six goals and was voted Gillingham’s player of the year. He was also a rock defensively during that campaign.
Why did he depart in the summer?
This is worth separating from his previous contract situation.
Masterson had actually signed a new one-year deal in June 2025, keeping him at Gillingham until summer 2026.
He was subsequently released at the end of the 2025/26 season, as part of a major Gillingham squad clear-out. We finished 17th in League Two for a second successive season and released 16 players. Masterson was among those departures.
The big mitigating factor was availability. He suffered the longest injury of his career and missed roughly four months. He only managed 12 league appearances and 751 minutes in 2025/26, although he did return in December and scored twice.
So I wouldn’t characterise the departure as “Gillingham didn’t rate him”. Rather, he was coming off a season in which he had been unavailable for a substantial period, and we were looking for a huge overhaul.
What style of defender is he positionally/tactically?
He’s a traditional centre-half rather than an aggressive, front-foot stopper.
The strongest evidence from his Gillingham career is his positional awareness and reading of the game. Qualities that have been commented on when he signed permanently.
He’s right-footed and primarily a centre-back. His height and positioning make him particularly useful in a defensive structure where he can:
Read the danger early rather than constantly having to recover
Defend his box and deal with crosses
Use his size in aerial situations
Step in for interceptions
Organise the players around him
He’s also not simply a ‘defend first, clear it’ player. His background at Liverpool and Queens Park Rangers means he’s been exposed to possession football, while at Gillingham he was comfortable enough to contribute to build-up and set pieces.
I’d call him a composed, positionally intelligent central defender who likes to read the game rather than chase it.
What are his main strengths?
1. Reading of the game/positioning. Probably his biggest asset. He has repeatedly been praised for positional awareness.
2. Aerial ability and physical presence. He’s a big centre-half and gives you a genuine presence in both boxes.
3. Leadership. This developed into a significant part of his game. Even when Masterson was injured, Gareth Ainsworth talked about getting his “leadership” back into the team.
Masterson himself has spoken about learning leadership qualities from players such as James Milner and Jordan Henderson during his Liverpool days.
4. Goals from centre-back. Six in 48 appearances in 2023/24 is an excellent return for a centre-half.
5. Temperament/professionalism. His interviews are consistently positive. He talks about responsibility, improving himself and helping the team, rather than complaining about circumstances.
How about weaknesses?
The biggest question isn’t really talent – it’s availability.
His 2025/26 season is the obvious warning sign: just 12 league appearances after a four-month injury lay-off. His career record also isn’t one of consistently playing 40-plus games every season.
On the pitch, I’d be cautious about expecting him to be a dominant, ultra-aggressive defender who will single-handedly erase problems behind a high defensive line. His game is more about anticipation, positioning and organisation than spectacular recovery defending.
Equally, while he has experience above League Two – including Championship football with QPR – the bulk of his recent football has been at League Two level. That’s something Reading will have to take into account.
What are your stand-out memories of him for good or bad reasons?
The obvious one is 2023/24, when he was Gillingham’s player of the year after 48 appearances and six goals. That was the season when he really established himself as one of the club’s most important players.
Another memorable aspect was how much he connected with the supporters. In 2025 he said he had a particular connection with the Gillingham fans and that he had played his best football at the club.
Then there’s his return from injury in December 2025. He described getting back into competitive football as an amazing feeling and thanked the club and supporters for their backing during what he called the toughest injury of his career.
The negative memory is therefore less about a particular bad performance and more about the frustrating injury-hit final season. He had just signed a new deal, but ended up contributing relatively little before being released.
What’s his character like?
He’s very well regarded.
Masterson comes across as serious, ambitious and team-oriented. He clearly cares about the cl...
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