So for those of you looking for a little bit of a football fix, we at the Chron are putting together a regular little quiz, focusing on a Town campaign of the past - and it's just a bit of fun.
Today, we are heading to the season from summer 2004 to May, 2005.
The Scot later admitted he had been a little hasty in some of his decisions.
The fact he allowed central defender Ian Sampson to retire and central midfielders Chris Hargreaves and Paul Trollope to leave, saw a lot of experience discarded, and with skipper Paul also being sold to Barnsley a few weeks before the start of the season, it left a big hole in the middle of the team.
And at the beginning of the new campaign, despite a bright start that saw them win their two opening games, too many teams went riding straight through the middle of it, with an early-season injury to summer signing David Rowson proving pivotal.
There was a particularly painful afternoon as old foes Mansfield, who after seeing off the Cobblers had lost the play-off final to Huddersfield Town on penalties, dished out a 4-1 hammering at Field Mill in early September - with another of Calderwood's rejects, Derek Asamoah, scoring the opener.
But the return of Rowson and the mid-September signing of Lee Williamson, surprisingly out of favour and surplus to requirements at Keith Curle's Mansfield, proved to be a masterstroke as Town's fortunes changed dramatically.
With their new found steel in the middle of the pitch, and another summer signing, Scott McGleish, banging in the goals up top, they went on a streak that saw them surge from 16th in the table in October to fifth by the end of December.
Automatic promotion was looking a possibility.
But from mid-January, results were mixed and the team looked like they were going to even miss out on the play-offs as they suffered three defeats in a row in April.
That left them eighth with three games to play... but thankfully they found their mojo to see off Lincoln, Chester City and Kidderminster to seal seventh and, for the second year running, a place in the play-offs.
There opponents would be a Southend United team who had done the double over them in the league - and they were to prove just too strong in two disappointing play-off games as well.
Town drew a drab first-leg at home 0-0, before going down 1-0 in an equally uninspiring Saturday evening match at Roots Hall.
The match was Sky Sports' dessert offering following the main course of Arsenal's FA Cup Final win over Manchester United, but there was nothing sweet about it as a Freddy Eastwood penalty proved to be the difference.
The defeat meant more play-off woe for Calderwood and his assistant John Deehan, although this time without the drama, and another summer of stewing over what might have been, before regrouping for the new campaign.