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City took an early advantage when Adrian Littlejohn scored his first goal for the club, beating Paul Bastock in the Pilgrims goal.
Ex England legend Paul Gascoinge scored a terrific free kick on 18 minutes to make it 1-1, but seconds later West Ham loanee Greg Pearson emulated the star by curling in his own superb dead ball. 2-1 it remained untill half time despite some entertaining stuff from both sides. Simon rayner had to pull off good saves from journeyman striker Martin Carruthers and Northern Ireland International Andy Kirk.
At half time Bostons star attraction 'Gazza' was replaced by Tom Williamson.
City opened the second half brighter and on 61 minutes city youngster Adam Kerley made it 3-1, beating two defenders before firing home. Along with Leon Mettam and and Lee Frecklington the youngster looked every bit a professional which will encourage home fans.
Boston then staged a remarkable comeback, with Matt O'Halloran and Martin Carruthers (2) putting them into the lead at 4-3. It looked like they had performed their second comeback of the week against fierce rivals.
However they hadn't banked on Kerley. The youngster managed to stab home a cross from veteran Adrian Littlejohn to level the scores.
The final whistle signalled a penalty shoot out. Greg Pearson hit the bar for City in sandwiched between misses for Lee Thompson and Danny Thomas. City right back Dean West fired home the final kick to put City into the final against Scunthorpe United.