Yeovil Town made it four years without a win in the Johnstone's Paint Trophy when they lost by three goals to two against Bournemouth at the Seward Stadium.
The Glovers went three goals behind after just half an hour thanks to a Marc Pugh brace and an own goal from Curtis Haynes-Brown. But a better second half performance saw goals from Steve MacLean and Max Ehmer reduce the arrears and MacLean was unlucky to hit the post in stoppage time as the Glovers looked to force penalties.
Manager Terry Skiverton made five changes to the team that lost 3-1 at home to Bury on Saturday. Luke Ayling and Ed Upson both dropped from the squad following suspension for reaching five bookings while Nathan Jones, Kieran Agard and Steve MacLean dropped to the bench.
In their places came Kerrea Gilbert, Curtis Haynes-Brown and Bondz N'Gala with Oli Johnson and Gavin Massey being promoted from the bench.
Max Ehmer, of all people, hooked a shot over the bar on seven minutes as the defender turned midfielder looked to notch his first Glovers goal and Massey just failed to make proper contact with the ball after Cherries keeper Shwan Jalal had dropped the ball.
On sixteen minutes, the home side took the lead through the dangerous midfielder / top scorer Marc Pugh. Striker Steve Fletcher headed a cross down and Pugh acrobatically finished with his left foot.
Nine minutes later, it was 2-0 and Pugh was again the scorer. Fletcher was again involved with a header on to the midfielder and as Jed Steer advanced, his clearance rebounded off Pugh giving the Cherries star the simple chance of tapping home.
If the travelling Glovers thought it couldn't get any worse, it soon did when number three went in on the half hour. Again Pugh was involved as his cross was nodded into his own net by Haynes-Brown under pressure from Fletcher.
Fletcher and Massey then exchanged chances at either end and the half closed with more trouble for Town when Kerrea Gilbert crumpled after attempting a run along the flank.
He was replaced at half time by striker MacLean and after Ehmer and Johnson had seen shots saved by Jalal, MacLean pulled a goal back on 64 minutes when he turned and fired home with his right foot.
Skiverton shuffled his pack bringing Agard and Anthony Edgar on for Alan O'Brien and Johnson but the next chance came at the other end when Steer pushed a Pugh shot over the bar.
With two minutes left, goalscorer MacLean turned provider when his low cross was tapped in on the six yard line by Ehmer for his first ever Yeovil Town goal and even after that, MacLean almost grabbed a sensational equaliser from a stoppage time corner but his flicked header rebounded off the post.
More late pressure from the visitors saw Adam Barrett head an Edgar shot over as Town pressed desperately for the leveller but it just wouldn't come and the Glovers search for a win in this competition continues.