Despite taking a fourth minute lead through Liam Davis the Glovers returned to Somerset empty handed. Grant Leadbitter and Albert Adomah ensured the hosts went into half time with a slender lead.
Just after half time Jacob Butterfield made it 3-1 to the home side with a well struck effort from 25-yards. With 15 minutes remaining Boro made it 4-1 when Kei Kamara headed from from a corner.
Town had the dream start when after just four minutes Davis opened the scoring.
Boro skipper Rhys Williams let the ball go past him, but Davis outpaced the centre-back to race clear and fire the ball under the advancing Steele and into the net.
The home side were level just four minutes later when Leadbitter volleyed home an Adomah cross from just inside the penalty area.
Minutes later the hosts thought they had taken the lead but were denied by the woodwork twice within ten seconds.
Winger Kamara found himself unmarked at the back post but his first header rebounded off the crossbar. The ball found its way back to the midfielder but his second attempt came back off the post and the Glovers managed to clear their lines.
The home side took the lead after 24 minutes. A superb pass by Whitehead split the Yeovil defence and found Friend. The left back got into the box and was upended by Grant leaving referee Whitestone no option but to point to the spot.
Leadbitter stepped up but saw his penalty superbly tipped onto the post by Hennessey, but former Bristol City man Adomah was on hand to put the rebound over Hennessey and into the net.
Gary Johnson made a sub after 32 minutes with Sam Hoskins replacing Andy Williams.
The Glovers thought they had levelled the scoring after 35 minutes when Steele parried a Grant shot into the path of Madden, but Boro were saved when the assistant’s flag denied the Irishman.
Johnson made his second sub at half time with Kieffer Moore replacing Madden.
Boro extended their lead five minutes into the second half when Butterfield’s 25-yard shot flew past Hennessey and into the corner of the net.
Substitute Hoskins had a great chance to reduce the deficit on 53 minutes. A quick break from Davis on the left saw him square the ball to the unmarked Hoskins. The former Southampton man beat Steele to the ball but saw his effort rebound off the post.
With just over 15 minutes remaining Boro made it 4-1. Kamara headed home from a corner that was whipped in from the left, leaving Hennessey with no chance.
In the last five minutes Moore had a golden opportunity to pull a goal back but somehow only managed to loop his effort into the hands of Steele.