A sucker punch from Wycombe Wanderers saw Town suffer defeat at Huish Park in Sky Bet League Two.
In a first half in which the Glovers did well to pinback their promotion-chasing opponents, Otis Khan went closest to opening the scoring when his free-kick came back off the bar just before the break.
Looking the most likely to open the scoring Town thought they had when Alex Fisher poked in from close range just minutes after the restart, only for the linesman's flag to rule it out for offside.
Going close yet again, Tom James saw a free-kick from 25 yards clip the post before Randell Williams won it for the Chairboys with their only shot on target as the game ticked towards the final 10 minutes.
Reverting back to 4-4-2 from the start after a change in shape at Swindon in midweek, Darren Way made three changes for the visit of Wanderers.
Ruled out for the remainder of the season, Stuart Nelson was replaced by Jonny Maddison between the sticks allowing goalkeeper coach Steve Phillips a spot on the bench.
In defence, Ryan Dickson returned from suspension for Bevis Mugabi whilst Jordan Green regained a starting spot at the expense of Alefe Santos who started amongst the substitutes.
Partnering the in-form Fisher upfront, Green was in the thick of it from the off receiving lengthy treatment after a coming together with Adam El-Abd before colliding with visiting stopper Scott Brown as the pacey 23-year-old looked to make an impact.
Although both sides displayed plenty of attacking intent, goal scoring opportunities remained elusive as a flurry of corners and balls into the final third couldn't be turned into chances.
However, that changed five minutes before the break when the hosts almost stormed into a two-goal lead.
Captain Omar Sowunmi headed just wide from Lewis Wing's hanging ball into the box before Khan was only denied by the fingertips of Scott Brown who did well to tip the winger's wide free-kick onto the underside of the woodwork.
Finishing the opening 45 minutes strongly, Way's side looked on course to continue their good run of form against the division's top six and almost started the second half in perfect fashion.
Green showed his pace to create half a yard to steer in a low cross for Fisher to tap in, only for the offside ruling to cancel out what would've been the opener.
Remaining on the front foot, Rhys Browne became a thorn in the side of opposite number Joe Jacobson as he twice threatened to get shots off on goal, before the Chairboys registered their first meaningful attempt on goal after 63 minutes.
Nick Freeman found a pocket of space 25 yards out but could only power a low drive just wide of Maddison's goal as Gareth Ainsworth's side struggled to get going.
Having gathered momentum in the second half, the Glovers struck the woodwork for a second time with a little under 15 minutes remaining.
Tom James' free-kick from all of 25 yards had Brown beaten but to the visiting keeper's joy it clipped the post and landed wide.
With all signs pointing towards a Yeovil winner, Wycombe stunned the hosts by taking the lead with their first shot on target with 79 minutes on the clock.
Jacobson's wide free-kick was recycled by Wanderers, allowing Marcus Bean to tee up Williams whose side-footed strike from just inside the box nestled in the corner of the net.
Keen to salvage the point they at the very least deserved Way introduced Ryan Seager and Santos from the bench as caution was thrown to the wind, but Town couldn't find a second late equaliser of the week and suffered just their second defeat in six.
Yeovil Town: Maddison; James, Sowunmi, Donnellan, Dickson; Browne (Barnes 67'), Wing, Gobern (Santos 85'), Khan; Green (Seager 83'), Fisher.
Subs not used: Phillips, Mugabi, Whelan, Bird.
Wycombe Wanderers: Brown; Harriman, El-Abd, McGinley, Jacobson; Bean, O'Nien (Williams 32'), Gape; Kashket (Mackail-Smith 59'), Akinfenwa, Freeman (Tyson 76').
Bookings: Bean 74', El-Abd 75'
Subs not used: Ma-Kalambay, Bloomfield, Saunders, Cowan-Hall.