DEFEAT is always painful, but this will hurt Town Juniors all season.
The dominant side for long spells, Town crashed to a sloppy set piece and a 30-yard thunderbolt at York Street last night.
A crowd of 345 watched John Dungworth's side miss some gilt-edged chances - just like the first round against Rochdale - only this time they were made to pay.
Town had little luck, either, and when James Hand's incredible dipping drive smashed against the underside of the bar only for Gavin Huxall to head the rebound over from close range on 58 minutes, you just got the impression it wasn't going to be their night.
So it proved, and despite fine work from Tom Clarke at the back and plenty of industry in midfield and up front, Town were out.
Boston will now go to Barnsley in the third round (the Oakwell lads beat Hartlepool 2-1 last night) while Town are left to reflect on what might have been.
Boston's winner, a brilliant left-foot drive from Jay Mahoney in the 76th minute, was a stunner in more ways than one.
Not only did Under 16 keeper Simon Eastwood have no chance whatsoever as the ball seared beyond him and in off a post, but it came after Town had been pressing all half to build on Daniel Highley's equally spectacular equaliser.
That had come barely 53 seconds into the second half and was dipped into the corner from 25 yards with keeper James Lambley off his line.
Despite controlling the opening stages of a gripping tie and creating plenty of pressure, Town were rocked when going behind in the 34th minute.
Firstly, keeper Eastwood, who had earlier saved well from Mahoney, touched away a shot from Zac Loader after Daniel Racchi had given away possession just outside the box.
From the resulting corner, however, Town allowed centre-back Keith England to rise unchallenged and power home from six yards.
Hand was unlucky not to redress the balance just before half time with a blistering shot which was tipped over the top, only moments after Dungworth made a smart tactical swap to put Highley alongside Huxall up front.
It looked like it would pay off in a powerful opening 20 minutes of the second period, but after Hand and Huxall had gone close and the latter had been denied a penalty, Town missed the boat on 66 minutes.
Firstly, hard-working Joe Shaw was denied superbly from close range and then, with the goal at his mercy, Matthew Biddle fired over from three yards out.
Town - Eastwood, Wilson, Evans, Racchi, Clarke, Walls, Highley, Shaw, Huxall, Biddle, Hand. Subs not used: Beck, Smithies, Berrett, Melcher, Skarz.