Contract Crossroads: Seven Ipswich Town Stars Nearing the End of the Road
Following their painful exit from the Premier League last season, Kieran McKenna’s Ipswich Town entered the current campaign with a singular, clear-cut objective: securing an immediate return to the world’s most lucrative division. While the Tractor Boys haven’t spent as much time in the automatic promotion spots as some pundits predicted, they have successfully maintained their status as a persistent threat in the promotion race throughout the year.
The January transfer window was a relatively quiet affair at Portman Road, with the club only securing senior signatures for Anis Mehmeti and Dan Neil. Despite an exhaustive search for a new frontman to bolster the attack before the deadline, the club ultimately failed to land a central striker. To balance the squad, several notable names including Cameron Humphreys, Harry Clarke, and Sammie Szmodics were sent out on loan for the duration of the season. As it stands, Ipswich appears well-positioned for a late-season surge toward the top two, but the looming expiration of several player contracts adds a layer of administrative tension to their promotion charge.
According to data from Transfermarkt, seven players currently on the books in Suffolk are set to become free agents this summer. With the club’s divisional status for next year still a mathematical mystery, we take an in-depth look at the individuals who may be playing their final months for the Tractor Boys.
Ashley Young
Now 40 years of age, Ashley Young is undeniably entering the final chapter of an illustrious professional career. The former Aston Villa and Manchester United standout has defied the typical aging process by maintaining elite fitness levels, successfully transitioning from a marauding winger to a dependable full-back as his pace naturally declined. Boasting an incredible resume of over 750 career appearances spanning the Premier League, Championship, Serie A, and the Champions League, Young joined Ipswich last summer primarily to provide veteran cover. However, he has found starts hard to come by, featuring in the opening lineup just three times this season. Given his age and his current role as a fringe player, it is highly improbable that he will be offered an extension, though the player himself has yet to confirm if he will hang up his boots for good this June.
David Button
Continuing the theme of veteran experience, 36-year-old David Button has spent the current campaign serving as the third-choice goalkeeper behind Alex Palmer and Christian Walton. Having joined on a free transfer during the summer window, Ipswich represents the 19th different club of Button’s nomadic career—a journey highlighted by a successful three-year stint at Brentford a decade ago. The likelihood of a contract extension for Button appears to be a toss-up; it may depend entirely on whether Ipswich secures promotion and whether Kieran McKenna feels his leadership in the dressing room justifies a spot on the wage bill. As of now, Button is on track to depart Portman Road without having recorded a single minute of competitive action for the club.
Conor Townsend
Conor Townsend arrived in Suffolk from West Bromwich Albion following the club’s promotion to the top flight, intended to be a direct competitor and high-quality backup for Leif Davis at left-back. Unfortunately, his time at Ipswich has been nothing short of a nightmare. After making over 200 appearances for the Baggies, Townsend’s momentum was halted by a devastating ACL injury during pre-season that sidelined him for the vast majority of the year. He has managed just six league appearances since his move. By the time his contract expires this summer, he will be 33 years old and recovering from a major injury, making it almost certain that the club will look to move in a younger direction rather than offering him fresh terms.
Wes Burns
Now in his fifth season with the club, Wes Burns is a bona fide fan favorite at Portman Road. He played a pivotal role in the historic journey from League One to the Premier League, providing pace and goal threat from the flank. The Welsh international has recently fought his way back from a significant layoff following knee surgery and will be desperate to contribute to the promotion push in these final weeks. However, at 31, Burns faces an incredibly crowded pecking order. With talents like Anis Mehmeti, Sindre Walle Egeli, Jack Clarke, Kasey McAteer, and Jaden Philogene all vying for minutes, his path to the starting XI is blocked. While his departure seems likely, it isn’t a settled matter; if Burns can produce a moment of magic before May, his experience might convince McKenna to keep him around.
Conor Chaplin
Much like Burns, Conor Chaplin is a hero of the club’s rapid ascent through the English divisions. However, the arrival of high-profile competition such as Marcelino Nunez and Chuba Akpom saw Chaplin slip down the ranks, leading to a loan move this season. He returned to his boyhood club, Portsmouth, in the Championship, but he has struggled to replicate the talismanic form that once made him the first name on the team sheet in Suffolk. At 28, Chaplin should be entering his prime, but his future with Ipswich is precarious. Having struggled to make an impact at the Premier League level previously, his stay likely depends on whether Ipswich remains in the Championship. If he does leave, he will be remembered as one of the club’s greatest bargains, having cost just £750,000 back in 2021.
Cameron Humphreys
A graduate of the Ipswich youth system, 22-year-old Cameron Humphreys has found it difficult to cement a permanent place in Kieran McKenna’s tactical plans. Following a successful loan spell at Wycombe Wanderers in League One last season, he was sent back to that division this month to join Huddersfield Town. Humphreys is a talented technician, but the sheer depth of the Ipswich midfield—featuring Jack Taylor, Jens Cajuste, Dan Neil, and Azor Matusiwa—means his path to the first team is effectively obstructed. Should Ipswich return to the Premier League, the gap in quality will likely only widen, making it increasingly probable that Humphreys’ future lies away from his home club.
Harry Clarke
As a lifelong Ipswich supporter, Harry Clarke’s journey back to the club was a fairytale. After developing in Arsenal’s academy and gaining experience through four different loan spells at clubs like Stoke City and Hibernian, he returned home to help his club achieve back-to-back promotions. Despite his emotional connection and past contributions, his recent game time has been severely restricted by recurring injuries and the form of other right-backs. Now 24, Clarke is currently spending the second half of the 2025/26 season on loan at Charlton Athletic under Nathan Jones. His goal is simple: play enough minutes to prove his fitness and quality, either to earn a new contract at Portman Road or to attract a new permanent home in the summer.
