Oxford United may be loving life in the Championship at the moment, but it’s fair to say that they have been through a lot in recent seasons to get there.

The U’s were last in the second tier of English football back in 1999, and in the 25 years that followed they dropped out of the Football League completely, before slowing working their way back up through the divisions.

One man who played an important role in the club’s resurgence was Chris Wilder, with the current Sheffield United boss spending six years at the Kassam Stadium, having his first foray into EFL management during his time with Oxford.

Wilder joined The U’s in December 2008, initially on a caretaker basis, after six years at fellow non-league side Halifax Town, and while the 57-year-old will be fondly remembered for helping the club back into the EFL, there was no happy ending for him.

Ian Lenagan’s Chris Wilder decision didn’t pay off in 2013

After taking over in 2008, Wilder just missed out on the National League play-off places for the 2008/09 season, but they went one better the following season.

He led the club back to the EFL after a four-year absence in 2010 after winning the play-off final against York City, and he quickly helped them become a stable club in League Two over the course of the next couple of seasons.

The U’s finished 12th, 9th and 9th in their first three seasons at League Two level, but some supporters wanted more, and felt like things had gone stale under Wilder, as summed up by finishing in 9th place in two consecutive seasons.

It looked as if Wilder had perhaps taken the club as far as he could, but Ian Lenagan, the club’s chairman at the time, rewarded him with a new one-year deal, a decision that wasn’t too popular with some supporters.

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Many of the Kassam Stadium faithful appreciated what he’d done for the club, but felt that giving him a new contract was a step backwards, and so it proved.

The 2013/14 season actually got off to a good start for Oxford, and they looked like they could finally break into the play-off places they’d missed out on in previous seasons, but Wilder resigned in 2014, moving to League Two rivals Northampton Town instead.

Moving to a direct league rival was a controversial move, and it meant there was no happy ending for Wilder at Oxford after Lenegan had given him a new deal.

However, in hindsight, Wilder leaving the Kassam Stadium proved a good move for both parties over the course of the next couple of years, and they’re set to face off in the Championship this season, a far cry from their days in League Two.

Chris Wilder’s decision to leave Oxford United proved mutually beneficial

In the next couple of years that followed his Oxford United departure, Wilder would manage in all four divisions, culminating in a top-half Premier League finish with Sheffield United during the 2019/20 season.

He helped Northampton win promotion to League One during the 2015/16 season, winning the title, before taking over at boyhood club Sheffield United, where he led them from the third tier of English football to the Premier League in just three seasons.

He left the club in March 2021 but returned last season after spells with Watford and Middlesbrough, and he currently has the Blades competing in the upper echelons of the Championship table.

Meanwhile, Michael Appleton led Oxford to League One in 2016, and after eight seasons in the third tier, Des Buckingham led the club to the Championship in 2024, a hugely impressive feat which not many people saw coming.

Wilder’s time at the Kassam Stadium certainly didn’t have a happy ending, but both him and Oxford United enjoyed success in the years that followed, and his decision to depart seems to have mutually benefited both parties.

He’ll return to Oxford United in April when his Blades side travel to the Kassam Stadium, and it’ll be interesting to see how he’s received by The U’s faithful.

In hindsight, Lenegan should have allowed Wilder to leave in the summer of 2013 instead of giving him a new deal, and him leaving midway through the next season perhaps tarnished his legacy somewhat.