Bolton Wanderers promotion will be bittersweet for 30-y/o - Trotters exit surely looms | OneFootball

Bolton Wanderers are back in the Championship after an absence of seven years, but this might not be good news for all the players who go them there.

Bolton Wanderers are celebrating their return to the Championship following an absence of seven years, but this could be bittersweet news for a player who's been part of the journey back from the brink.

In the end, the League One play-off final couldn't have gone much better for Bolton Wanderers. Level at half-time against Stockport County, three second half goals resulted in a 4-1 win and a return to the Championship following an absence of seven years.

The result of this can only be framed as a vindication of the club's decision to hire Steven Schumacher in January 2025. The former Plymouth manager was unable to get the club into a play-off place at the end of the 2024-25 season, which ended with them in 8th place in the table.

But over the course of 2025-26 his team was in the top six consistently from the first weekend in November, and with a 2-0 aggregate win against Bradford City coming on top of their comfortable win in the final against Stockport, they negotiated their way through the play-offs with three wins from three matches.

Kyle Dempsey could find himself coming to the end of the road with Bolton Wanderers

But for one player who's been a big part of that journey, victory in Sunday's play-off final will strike a bittersweet note. Dempsey has been a stalwart of the Bolton Wanderers team since his arrival at the club from Gillingham at the end of the January 2022 transfer window.

Over four and half years playing for the club, the midfielder has run up 161 appearances for the club, but at 30 years of age and with his contract at The Toughsheet Community Stadium due to expire in the summer, it might even be that being with the club as they secured a return to the Championship turns out to be his final act with the club.

The play-off final has resulted in a delay to the release of Bolton's retained list for the end of the 2025-26 season, but when it's published few would be that surprised if Dempsey was among those set to be released by the club.

Dempsey has only played half a season of Championship football over the duration of his entire senior career, and he played no role on the pitch as they secured their return at the end of the 2025-26 season.

Kyle Dempsey has become something of a League One specialist

Having only paid £150,000 for Kyle Dempsey at the end of January 2022, there's little doubt that Bolton Wanderers got full value for money out of the midfielder. But as the 2025-26 season headed towards its final stages he found it increasingly difficult to hold down a place in the first team, and he was overlooked altogether for selection in their play-off matches.

By the summer of 2023 - and despite an off-field incident which resulted in him having to wear an electronic tag for four months - Bolton had seen enough of him to warrant extending his contract, but that contract expires this summer.

This is problematic for Dempsey because he is something of a League One specialist. His senior career started at Carlisle United in 2014, but the vast majority of his time since then has been spent in the third tier, and he's only made 21 appearances in the Championship, all of which came during the 2015-16 season for Huddersfield Town.

But in the eventuality that he does leave the club, one moment will stand out among Bolton Wanderers supporters. Bolton's descent from the Championship to League Two came as a result of financial difficulties that nearly killed the club altogether, and the club's appearance in the 2023 Papa John's Trophy final against Plymouth Argyle at Wembley was a huge milestone in their recovery from this. Bolton won that game 4-0, and Dempsey scored their opening goal in that match.

With the player turning 31 years of age a few weeks into the new season, though, the likelihood of Kyle Dempsey being retained does not seem particularly high. But the good news for the player concerned is that, even if the club opt not to renew with him at the end of this season, his achievements at Bolton over the years should stand him in good stead to be picked up elsewhere this summer.