Despite an illustrious playing career, this was the charismatic Di Canio's first competitive game at Wembley and his team started today's final as favourites.
Chesterfield may be in a higher division but Swindon were the team in form and they dominated the opening 45 minutes with Lee Holmes closest to breaking the deadlock
But the second half was less than a minute old when disaster struck. Oliver Risser stuck out a leg and steered the ball into his own net to give Chesterfield the lead.
Swindon continued to enjoy long periods of possession but they just couldn't force an equaliser, although Alessandro Cibbocchi forced a brilliant save from goalkeeper Tommy Lee in the 88th minute.
With the game deep into stoppage time, Swindon dreams were finally shattered when Craig Westcarr broke clear to score Chesterfield's second.