When the one-time Wimbledon centre-forward was appointed manager of his home town club two and a half years ago, Whaddon Road was one of football's outposts, on the Dr Martens League beat. Come 7 August, it will be on the Nationwide map. Rochdale may not be the most attractive of visitors but their presence, in the shadow of Cleeve Hill, will nevertheless confirm that Cheltenham is in the national sporting hunt for something other than horse-racing kudos.
"It's unbelievable, really," Cotterill pondered. "For Cheltenham Town to be in the Football League, and in the League Cup, playing against Norwich City... it's something you just wouldn't have imagined. But it has happened. And we've got to get on with it."
Cotterill has been getting on with it impressively, too, it has to be said. He has overseen the summer transition of his squad from part-time to full-time with the same shrewdness that transformed Cheltenham from Southern Leaguers to Conference champions, and with a prudence that will not have passed without appreciative note in the boardroom.
In selling Jason Eaton to Yeovil for pounds 15,000 and buying Hugh McAuley from Leek Town for pounds 20,000, Cotterill has replaced a 29-year-old striker who scored 10 goals last season with a 22-year-old who scored 20 - at a cost of pounds 5,000. "We're also in the process of selling Dennis Bailey to Kingstonian or Forest Green for pounds 15,000," he said, "and we've got a 21-year-old goalkeeper, Steve Higgs, ex-Bristol Rovers from Worcester for pounds 10,000. So at the moment we've raised pounds 30,000 and spent pounds 30,000. We're quits.
"We haven't spent a lot in the past two years. We've still got four or five of the players we had in the Dr Martens League and the players we have bought have been predominantly around the pounds 15,000 mark. We're hoping now that those pounds 15,000 players will hold their own in the Football League. I'm sure some will and perhaps some won't. And some we got for nothing will probably be up to the mark, too."
Those for whom the jump to Third Division football was deemed a step too far have been released, Cotterill putting practicality ahead of sentiment in adding Clive Walker's name to the list. "Clive is 42," he said. "He came in and did a very good job for us but it would have been more difficult for him to play full-time football."
Cotterill himself is only 35 - a young man in the football management game but already a veteran achiever. His playing career cut short by injury, he guided Sligo Rovers into the Uefa Cup, with their highest ever League of Ireland placing, before applying his managerial Midas touch to Cheltenham. In four months he dragged the club from the bootlaces of the Dr Martens League. In his first full season he took them to the runners-up spot behind Halifax in the Conference and to victory in the FA Trophy final against Southport at Wembley. Then came last season's successful graduation campaign.
"I learned a lot from the men I played under," Cotterill said, considering his managerial make-up. "Bobby Gould, Ray Harford, Joe Kinnear, Peter Withe, Tony Pulis... You take a little bit from all of them, I think, and then there's a large chunk of yourself. I speak to some very good people in the game if I need bits of advice. Harry Redknapp has always been very, very good with me and I speak to Tony Pulis a lot, and to John Ward. They're all good people."
Not that Cotterill appears in need of help as he prepares to take Cheltenham into the Football League - via a training camp in Gottingen, Germany, this week. "As a Cheltenham lad I was proud to lead the team out at Wembley for the FA Trophy final," he said. "And obviously it'll mean a lot to me to lead the club into the Football League. It's been a dream, really. But it's important that we don't get carried away with it all.
"Just because we've done well in the Dr Martens League and in the Conference, we can't think we're going to take the Football League by storm. We must make sure we keep our feet on the ground and have a good look at the Third Division before we start talking about making too much headway."
Too much more headway, that should be. Cheltenham Town have already come a long, long way in a short space of time with the tracksuited builder of their Football League dream.