Not only did it signify the loss of an influential midfielder who scored on fifteen occasions last term, but it rubbed even more salt into Town's healing play-off wound in the sense he left for absolutely nothing - not even a blasted penny.
But they do say every cloud has its silver lining, and that silver lining in this case is Owen Garvan - sweet seventeen and already a crucial part of Joe Royle's ever changing jigsaw puzzle at Portman Road.
He's energetic and he's threatening - never afraid to shoot and his goal against the Saint's was exquisite, a pure touch of class.
He is the legs in a midfield consisting of several oldies including Magilton, Horlock and Currie. Without Garvan and the injured Westlake, Town's midfield would be just as fast moving as the Alf Ramsey and Bobby Robson statues outside the ground - we probably wouldn't stand a chance!
In the midst of the Turf Moor Shambles, Garvan was the inspiration. Committed and keen, something the rest of the squad weren't not for long periods against Crewe.
Royle believes Town have made an "outstanding" start to the season considering the number of injuries and suspensions Town have had.
Few could disagree, but Garvan has made the step-up to first team look as easy as what the Premiership appears to be for Darren Bent.
Joe must be delighted with him. So why don't we hear him singing his very much overdue praises? Maybe it's because he doesn't want to alert other Premiership managers to his services, and who could blame him? He's a future Town captain in the making.... if he's still here that is.