Quick Read
- Freddie Ladapo has signed with Chesterfield until the end of the 2025-26 season.
- He previously played for Huddersfield Town, Rotherham United, and Ipswich Town.
- Chesterfield is seventh in League Two and aiming for promotion.
Freddie Ladapo’s footballing journey is one of resilience, adaptability, and the relentless pursuit of goals—both on and off the pitch. Now, as the calendar turns to 2026, Ladapo finds himself at another pivotal crossroads, joining Chesterfield for the remainder of the League Two season. For fans of the Spireites and followers of English lower-league football, this signing brings fresh hope and a familiar story: a seasoned striker, hungry to prove his worth once again.
Ladapo’s move to Chesterfield comes on the heels of a challenging period. After a two-year stint at Ipswich Town—where he contributed to their competitive edge—he returned to Yorkshire with Huddersfield Town in the summer of 2024. Despite arriving with an impressive CV, including two League One promotions with Rotherham United, Ladapo struggled to find his rhythm in West Yorkshire. By September, his contract was ended by mutual consent, leaving him in search of a new club and, perhaps, a new chapter.
As reported by The Yorkshire Post and BBC Sport, Ladapo didn’t stay on the sidelines for long. Chesterfield, recognizing the opportunity, invited him to train as a free agent. His work ethic and attitude quickly impressed the coaching staff. First-team coach Gary Roberts noted, “He is a really good player. He is enjoying it, doesn’t miss a session, and he looks in really good shape. He has trained so well and it is nice to have him in.”
The winter transfer window, opening on January 1, 2026, saw Ladapo officially sign for Chesterfield, as confirmed by Yahoo Sports. The deal runs until the end of the current season, with Ladapo poised to contribute immediately to the club’s promotion ambitions. Chesterfield sits seventh in League Two, just outside the automatic promotion spots but very much in the mix as the season intensifies.
For Ladapo, the move is more than just another contract; it’s a chance to reignite his career and help a club with a clear vision. “It feels fantastic. It’s something that’s been a while coming. I’ve been training with the team for a little while now, so I’m glad that it’s over the line,” he told reporters. Ladapo describes himself as “an athletic striker with a keen eye for goal,” a reputation earned through years of stretching defenses, holding up play, and scoring crucial goals. Across stints with Colchester United, Crystal Palace, Plymouth Argyle, Rotherham United, and Ipswich Town, he’s amassed three promotions—a testament to his impact during high-stakes campaigns.
Chesterfield’s ambitions align perfectly with Ladapo’s personal goals. “Everybody has the goal of promotion in mind. I’m the same,” he said. The club’s decision to sign him is not just about numbers on a stat sheet but about injecting experience, hunger, and leadership into a squad looking to ascend. With the transfer window now open, Ladapo could make his debut on New Year’s Day against Oldham Athletic—a fixture that could set the tone for the remainder of Chesterfield’s season.
The signing comes at a moment when Chesterfield is actively strengthening its squad, with defender Malik Owolabi-Belewu also joining from Forge FC in Canada. Yet it’s Ladapo’s arrival that has garnered the spotlight, given his track record and the anticipation surrounding his potential impact.
For Ladapo, the pressure is familiar. He’s navigated promotions, relegations, and the uncertainties of football contracts. But the challenge at Chesterfield is distinct: help a club with history and ambition secure its place in League One. The fans will be watching closely, hoping his experience translates into goals and, ultimately, success.
There’s always an element of risk in mid-season signings. Will Ladapo rediscover his best form? Can he integrate seamlessly into Chesterfield’s system? The answers will unfold over the coming weeks, with each game a test and every goal a step closer to the club’s dreams.
Freddie Ladapo’s move to Chesterfield is more than a routine transfer—it’s a calculated gamble for both player and club. With the striker’s proven ability in promotion races and Chesterfield’s clear ambitions, this partnership could become one of the defining stories of the 2025-26 League Two season. If Ladapo delivers, it may just be the spark that propels the Spireites to new heights.
Sources: Yorkshire Post, BBC Sport, Yahoo Sports.