Chesterfield and the increasing challenge of League Two

Avoiding the trials and tribulations of the play-offs and instead going up automatically is the stated aim for Chesterfield next season, although it is not getting any easier.

Adding to the League Two mix for 2026/27 are York City and Rochdale, both fresh from 100-plus points promotions from the National League.

Among the quartet relegated from League One, Port Vale will expect to challenge and Rotherham United ought to be thinking the same now they’ve got ex-England manager Steve McClaren pulling the strings as Head of Football, even though they have yet to appoint a head coach.

And with resurgent Bristol Rovers, well-backed Salford and teams capable of kicking on like Grimsby, Barnet, Oldham, Crewe and Colchester, there will be no shortage of competition for the Spireites.

Rochdale join Chesterfield in League Two next season after coming through their National League play-off final against Boreham Wood at Wembley. Photo by Paul Harding/Getty Images)placeholder image
Rochdale join Chesterfield in League Two next season after coming through their National League play-off final against Boreham Wood at Wembley. Photo by Paul Harding/Getty Images)

“Not to be in the play-offs, to win the league, they’re the learnings (from last season),” said assistant manager Danny Webb.

"That’s the easiest thing to say but putting it into practice is hard because the league is getting tougher.”

Webb bases that theory partly on the length of time it is taking the big issues at the top to be decided.

"I feel in the last few years there hasn’t been anyone walking it,” he said.

Chesterfield celebrate a goal against Crewe before falling short in the play-offs. Pic: Brian Eyreplaceholder image
Chesterfield celebrate a goal against Crewe before falling short in the play-offs. Pic: Brian Eyre

"Bromley had to wait until right to the end, MK Dons similar, and Cambridge went up on the final day.

"The play-off positions also went right to the end with ourselves and Swindon, so it is more competitive.

"People might say that’s because the division is not as good because everyone is getting more points but at the same time we really wanted to use this opportunity this year to go up via the play-offs and it wasn’t to be.”

Chesterfield “didn’t turn up” in their play-off semi-final first leg against Walsall last year, lost 2-0, and left themselves too much to do.

Even though they were more diligent this year, the 1-0 deficit from the first leg was a killer against a Notts County side that found a steely defensive streak when it mattered most.

"Both seasons it has been the first leg,” said Webb.

"This year in the play-offs generally, whatever the league, the team that has taken the advantage in the first leg has gone on to qualify for the final.

“In our first leg there were things that didn’t go our way or things we didn’t take advantage of and sadly that regret will sit with us all for a little while yet.”

Can it be third time lucky for Chesterfield next season?

They should at least be encouraged by their year-on-year incremental improvement.

Added Webb: The positives for us were more league points and getting closer in the play-offs.

"We looked pretty solid in the last couple of months and the goals against column went from being not good enough to damned good.

"That is one of the many positives that will leak into our psyche as the days go on.”

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