The Pilgrims suffered a slender 2-1 defeat to League One side Rochdale to miss out on a home clash against Premier League giants Newcastle United in the process.
United trailed to Peter Crook's early own goal but levelled four minutes after the break through Jordan Thewlis, only to be dumped out by Aaron Morley's penalty with 11 minutes to play.
It was a fantastic night for the Boston public, with an attendance of 4,190 clocking through the York Street turnstiles to give Craig Elliott’s side super support from the outset.
They almost had the perfect start when Rollins rippled the outside of Roberto Sanchez’s net inside the first minute of the contest.
United’s evening took an unwanted twist three minutes later when Ian Henderson sailed a seemingly harmless cross-shot into the box, which was somehow spilled into his own net by CROOK.
Rochdale soon lost the services of Henderson to injury and United tried to up the ante, with Jonathan Wafula unable to hook home a Thewlis cross before Sanchez made a good near post save from Dominic Knowles.
The visitors could have doubled their lead three minutes before the break but substitute Rekeil Pyke slammed his effort against Crook’s far post when well-placed.
United were a different animal after the break and were level within four minutes. Wafula had already cracked the crossbar before getting his head on Alex Whittle’s return cross, with THEWLIS diving to power home a low header at Sanchez’s near post in front of a jubilant Town End.
The match was now evenly-poised, with Crook denying Matt Done and Pierce Bird heading over the crossbar from Martyn Woolford’s set-piece delivery.
Proceedings swung decisively in Rochdale’s favour in the 79th minute when Jay Rollins tripped impressive substitute Stephen Dooley in the box and MORLEY, dragged off in the first half during the initial tie at Spotland, buried the spot-kick low into the corner.
Boston (4-3-3): Peter Crook; Alex Penny, Luke Shiels, Pierce Bird, Alex Whittle; Jonathan Wafula (Jake Wright 83), Tom Platt, Martyn Woolford (Nicky Walker 90); Jordan Thewlis, Dominic Knowles (Simon Ainge 86), Jay Rollins. Subs (not used): Ashley Jackson, Karl Byrne, Shaun Tuton, George Willis (gk).
Rochdale (4-2-3-1): Roberto Sanchez; Luke Matheson, Eoghan O’Connell, Rhys Norrington-Davies, Jimmy Keohane; Jimmy Ryan (Stephen Dooley 66), Aaron Morley; Matt Done (Calvin Andrew 88), Callum Camps, Aaron Wilbraham; Ian Henderson (Rekeil Pyke 11). Subs (not used): MJ Williams, Kwadwo Baah, Fabio Tavares, Jay Lynch (gk).
Referee: Ollie Yates.
Attendance: 4,190 (234 visitors).