Leaving the FA Cup at the second round stage is not in itself unforgiveable – but the manner of Town’s exit will stand as a bitter memory in the minds of fans for years to come.
Chesterfield crashed out in the most humiliating fashion, shipping five goals and having a man sent off against League Two opposition.
Of course there are only seven places between the two sides in the football pyramid, but after back-to-back league wins, Wycombe Wanderers hauled the Spireites back to earth with an almighty bang.
Jon Nolan’s 64th minute sending off certainly assisted the Chairboys, but they were the better side all afternoon.
The movement and pace of their front three had Town’s defence chasing shadows and the home midfield was anonymous.
Up top, Chesterfield posed very few questions, keeper Jamal Blackman with little to do all afternoon.
At the other end Ryan Fulton was a busy man, several impressive and vital saves ensuring it didn’t get any worse for his side.
But even the keeper contributed to Town’s downfall, dropping a second half clanger.
Town simply weren’t up for the fight against a Wycombe side who started on the front foot and never took a backward step.
The writing was on the wall in the opening stages, Adebayo Akinfenwa making life difficult for anyone trying to mark him.
Scott Kashket, who went on to score a hat-trick, and fellow goalscorer Paul Hayes, played off the big man to great effect, making clever runs and leaving markers for dead.
Chesterfield players were drawn to Akinfenwa like moths to a flame, leaving gaps and space for his fellow Wanderers to exploit.
Not only that, the ball appeared to be glued to him at times as bodies bounced off him.
It was as good a forward display as Millwall veteran Steve Morison showcased earlier this season at the Proact.
Wycombe’s energetic performance matched the technical area antics of manager Gareth Ainsworth who headed and kicked every ball.
And their fans too were magnificent, admittedly having been given so much to cheer throughout, whereas the home fans were delivered a great big dose of disappointment.
Luke O’Nien had already brought a sublime save from Fulton with a 25-yarder before Wycombe opened the scoring.
Kashket’s wicked cross from the right was glanced in off the bar by the head of Hayes.
Wycombe had one foot in the third round when Dominic Gape’s cross was knocked down for Kashket to poke under Fulton.
Yes, there was a hint of offside about the goal, but it was typical of both sides that a man in white got to the ball ahead of a man in blue.
Wilson reacted by withdrawing Reece Mitchell and sending on Ched Evans, but even the Welsh international was powerless to change the tie.
Evans needed service and there was nothing forthcoming from the full-backs, the midfield or the creative players.
For Town mission improbable became mission impossible in the second half when Nolan lunged in needlessly on Gape and received his marching orders.
His manager called it a ‘stupid’ challenge and although at first viewing it perhaps looked worse than it was, what can’t be argued is how needless it was.
There just wasn’t a call for such a risky tackle on the touchline deep in Wycombe’s half of the pitch.
Nolan gave the referee the option of pulling out his red card – it’s not the first time he’s gone in with a wild one this season, but up to now he’s always got enough on the ball.
This time it cost him and his side dearly.
Wilson admitted Wycombe proceeded to ‘steamroll’ his side after that – it was all too easy.
A pass through the middle saw Kashket scamper clear for his second and after Fulton had made two fine stops, he came out for a corner and simply dropped it, Anthony Stewart finding the empty net.
Two minutes later the humiliation was complete, Kashket and last man Gary Liddle both falling to the ground - the striker first to his feet before a cool finish completed his hat-trick and a comprehensive rout.
A chance to plug some big financial holes was simply torn from Town hands in ruthless fashion.
As alarming as the scoreline and performance will be to Proact chiefs, the attendance certainly won’t provide a crumb of comfort, just over 3,000 Town fans deeming this a match worthy of their attendance.
It’s going to take some time and several very positive results to pick the mood up after this one.
Chestefield: Fulton 6, Liddle 4, Donohue 3, Evatt 4, Anderson 3, O’Neil 3, Nolan 3, Ariyibi 3, Mitchell 4 (Evans 32 4), O’Shea 3, Beesley 3 (Dennis 60). Subs: Allinson, Gardner, Dimaio, Simons, Maguire.
Wycombe: Blackman 7, Harriman 7, Jacobson 7, Stewart 8, Pierre 7, Gape 8 (Bean), O’Nien 8, Bloomfield 8 (Wood), Hayes 8, Akinfenwa 9, Kashket 9 (Cowan-Hall 81). Subs: Richardson, Jombati, Thompson, De Havilland.