When Gareth Ainsworth left Wycombe in February 2023, he left behind a club in transition, with club-legend Matt Bloomfield replacing him at the touchline.
Since then, the club has been through a lot of changes including new ownership, the club now owned by billionaire Mikheil Lomtadze, meaning they now have a lot more freedom than they did in terms of money compared to Rob Couhig’s ownership.
Wycombe have definitely been brave with their recruitment since Gareth Ainsworth left, his ‘rock and roll’ style of football now in the rear-view mirror, a handful of smart additions sometimes overshadowed by underwhelming signings who failed to live up to expectations.
From injury-plagued players way past their prime to forwards unable to find the back of the net and short-lived gambles on unproven players, the post-Ainsworth era has seen a lot of misses in the transfer market, and a few names stand out for all the wrong reasons.
1 – James Berry
Signing in January of this year for an undisclosed fee, believed to be in the region of £400k, James Berry joined Wycombe having managed to gain promotion three times in his past three seasons, Wanderers fans hoped he would have been able to do the same with the Chairboys in the 2024/25 season, making it four in a row for the player.
However, it never came to be. He only managed three appearances, playing a total of 34 minutes for the club.
Berry went on to rejoin his former club Chesterfield on a season-long loan deal for the 2025/26 campaign. A player with high expectations who never got the chance to live up to them.
2 – Richard Keogh
A 37-year-old centre back isn’t exactly what Wycombe needed during the 2023/24 campaign, lingering dangerously close to the drop come Christmas time.
Signing in July on a free transfer, he went on to make a total of 25 appearances for the Chairboys, but disappointed a lot of the time, being a shell of the player he used to be.
An example of a bad gamble on a player way past his prime, Keogh was released from Wycombe in January 2024, and it’s fair to say it wasn’t an emotional departure.
3 – Lyle Taylor
In November 2023, Lyle Taylor joined Wanderers on a short-term deal for free, and it’s fair to say he did absolutely nothing during his time in Buckinghamshire.
Making a total of nine appearances, seven in the league, one in the FA Cup and once more in the EFL Trophy, he scored no goals and didn’t look great whatsoever.
He was not up to the standard required and definitely had some issues with his attitude. He went on to join Cambridge United.
4 – Kian Breckin
Signing on loan from Premier League side Manchester City, hopes were high for the young player when he joined Wycombe Wanderers.
But again, he never really lived up to the standard required, making nine appearances for the club and never really making a proper impact in any of the matches.
5 – Harry Boyes
Another loan signing from the 2023/24 season and another player who was a profound disappointment and never lived up to the standards needed to fight for promotion that season.
Signing on a season-long loan in July, he went on to make 29 appearances for the club, assisting twice. In the match away to Barnsley in which Stryjek’s attempt at time wasting went horribly wrong as he was challenged by Sam Cosgrove, the Polish keeper falling over and losing the ball with Cosgrove converting into an open net, Boyes was shown a second yellow for dissent.
His loan was cancelled in January and he was loaned out again, this time to Fleetwood Town.
6 – Saxon Earley
A very interesting move overall, not because of the disappointment that came when he played, but because of the fact that he never actually played for Wycombe.
Signed on loan in February 2024 from Plymouth Argyle, he got injured and never made an appearance for Wanderers. Some even joked that he had gone missing in the Chiltern Caves.
7 – Alex Hartridge
Possibly a less obvious one compared to the above signings, Hartridge rejected a new contract at Exeter City and joined Wycombe on a free transfer.
He was sent off for allegedly time-wasting at Northampton in August 2024, and again with a clumsy challenge while already on a yellow against Blackpool.
He then returned to Exeter City on loan to Exeter City, returning to Wycombe before the start of the 2025/26 season, making a couple of appearances in the Carabao Cup in which he looked fairly solid, and many asked if he was on his way to redemption, but he left Wycombe and joined Burton Albion on deadline day.
