Swansea City crashed out of the Carling Cup after a bitterly disappointing display at Greenhous Meadow.
The Swans failed to find any sort of spark to clinch a place in the third round as League Two Shrewsbury deserved their Premier League scalp.
Swans boss Brendan Rodgers made nine changes to the side that picked up their first Premier League point in their history with a goalless draw against Wigan at the Liberty Stadium on Saturday.
Only striker Danny Graham and defender Ashley Williams remained in the side against the League Two outfit managed by Graham Turner.
There were starts for young defenders Daniel Alfei and Joe Walsh, with Alan Tate
skippering the side alongside Williams in the heart of the defence.
Joe Allen, Mark Gower and Andrea Orlandi started in midfield, with Leroy Lita and Luke Moore up front alongside Graham.
There was plenty of quality on the Swansea bench in Michel Vorm, Neil Taylor, Steven Caulker, Leon Britton, Scott Sinclair, Stephen Dobbie and Kemy Agustien in reserve.
Swansea City: Moreira, Alfei, Walsh, Tate ©, Williams, Allen, Gower, Orlandi, Lita, Moore, Graham. Subs: Taylor, Agustien, Sinclair, Britton, Vorm, Dobbie, Caulker.
Shrewsbury Town: Smith, Grandison, Jacobson, McAllister, Sharps ©, Cansdell-Sherriff, Wright, Wroe, Morgan, Ainsworth, Gornell. Subs: Neal, Collins, Leslie, Hazell, Richards, Bradshaw, Goldson.
Ref: P Tierney.
Att: 4,063. Away: 633
Both sides made a lively start with Swansea enjoying the early possession before the home side signalled their attacking intent.
A crunching tackle from Daniel Alfie on Joe Jacobson earned the Shrews a corner which Mark Wright curled towards the far post. But Jose Moreira did well to punch the ball clear under pressure.
Moreira was called into action again in the fifth minute when he did well to beat out a fierce drive from Marvin Morgan. The rebound fell to Terry Gornell, but the Portuguese 'keeper did well to push the rebound to safety with a double-save.
But it was Swansea who made the breakthrough in the 10th minute in bizarre fashion when Shane Cansdell-Sherriff headed the ball beyond Ben Smith under pressure from Danny Graham for a bizarre own goal.
Three minutes later and Shrewsbury could have been level when Morgan broke free down the middle again, but Moreira was equal to the task with a good save with his legs.
The equaliser duly arrived though in the 19th minute when Swansea failed to clear a Jacobson cross which eventually fell to Gornell on the right. And when he drilled in a low cross, Marvin Morgan arrived to fire home his third goal of the season from close range.
The game was still in the balance when Leroy Lita forced an easy save from Smith with 31 minutes gone, before the home crowd were up on their feet screaming for a penalty when Morgan, who was proving a handful for the Swansea defence, went down under a challenge from Joe Allen. But the referee quite rightly waved play on.
Lionel Ainsworth caused chaos down the right and when his cross flew across the face of goal, both Grandison and Morgan failed to apply the finishing touch before Nicky Wroe fired a deflected effort over the bar.
At the other end, Joe Walsh got up above the Shrewsbury defence, but his downward header bounced inches wide with 36 minutes gone.
Graham had a half-chance in the 43rd minute as Luke Moore flicked the ball on, but the striker was closed down quickly and his touch crept wide.
As the half came to a close, Swansea had regained control, but Shrewsbury were well worth a share of the spoils having created the better chances in the opening 45 minutes.
And to round things off, Morgan climbed all over Williams to head Joe Jacobson's cross against the bar.
Half-time: Shrewsbury 1 Swans 1
There were no changes from either side at the start of the second-half as Mark Gower fired an early effort over the bar.
There was far more urgency from Swansea now as Andrea Orlandi fired a free-kick into the Shrewsbury wall before Moore curled a 49th minute effort just wide.
Young Walsh had to be alert at the other end though as Ainsworth went racing clear only for the defender to time a perfect tackle.
It still wasn't happening for a sloppy Swansea though as manager Brendan Rodgers made his first change in the 65th minute as Neil Taylor replaced Walsh.
A minute later though and Taylor was in a side losing 2-1 as Shrewsbury took the lead when Gornell broke from the halfway line.
Gornell cut inside and looked to have pulled Joe Allen back. The referee didn't give the foul and when the ball was played across the edge of the box, Mark Wright drilled the ball beyond Moreira.
Swansea responded immediately by bringing on Stephen Dobbie for Orlandi.
Joe Allen tried to grab Swansea a lifeline in the 77th minute when his 25-yard drive forced Smith to push his fierce effort over the bar.
But time was quickly running out and with no sign of an equaliser, Scott Sinclair stepped off the bench to replace Moore with 11 minutes remaining.
It made no difference though as Shrewsbury wrapped the game up in injury time when Nicky Wroe drilled home a well worked free-kick from the edge of the area.
It completed a miserable and frustrating night for the Swans and the 633 travelling fans.