The Royals will travel North to face the Pilgrims at their York Street Stadium on either the 12th or 13th August in the Carling Cup First Round.
This season will be only Boston's second in the Football League, so, on paper at least, Reading will be clear favourites to progress to the next round. However, Alan Pardew's side have a dismal cup record.
Last season the Royals were defeated 3-1 at lowly Cambridge in the League Cup, worse followed in the FA Cup when Pardew's boys were knocked out in the Third Round by Walsall. Previously the Royals have suffered two embarrassing cup exits at the hands of York City. This years tie could, quite conceivably, see another 'shock' defeat for the 'favourites'.
Elsewhere, former Royals legend will start his Carling Cup career as a manager with a home tie against Plymouth. West Ham aren't used to entering the competition at the first round stage, but will enter early doors this season following their relegation from the Premiership. The Hammers face a home tie against Rushden.