Cambridge United fell to a 3-1 defeat at the hands of League One Southend United in their opening Checkatrade Trophy fixture at Roots Hall.
Despite several positive spells and a spirited performance throughout the evening from the U's, a second half brace by Shawn McCoulsky and a late strike by Isaac Hutchinson put the game beyond United who had initially taken the lead early in the second half through Reggie Lambe.
United lined up with seven changes as Mitov, Davies, Darling, Taylor, O'Neil, Osadebe, Azeez moved into the starting line-up for the U's.
Much like they had four days earlier in Stevenage, United began with a good pace to their play and caused the more threatening issues in front of goal.
Osadebe played a snappy one two pass with Jevani Brown on the edge of the Shrimpers 18 yard box to open up room for a cross, which looped up off a tracking Southend defender and landed fractions above the cross bar on 13 minutes. Brown's resulting corner whipped fiercely towards goal and required a goal line clearance from the hosts, as Joe Dunne's men increased the pressure.
As the half progressed, Brown, Osadebe and Azeez continued to cause Southend problems with a combination of slick passing and a sharp turn of pace.
Southend's first real opening came when Harry Bunn dispossessed Leon Davies on the right hand side on 24 minutes, and the winger's cross skewed off the shin of centre back Harry Darling whose interception was judged to perfection as it deflected wide and away from the impending danger inside the U's area.
That sparked the host's best spell of pressure in the first period, with Stephen McLaughlin going very close with a half volley from 20 yards half an hour into the game, which a full stretched Dimitar Mitov watched zip inches wide.
Southend continued to improve although failed to break the deadlock as the interval approached, with Darling forced to deny Shawn McCoulsky a one on one opportunity with Mitov before Bunn, John White and McLaughlin all fired efforts over from inside of the U's area.
However the final say of the first half went to George Maris, when the midfielder's finely struck effort from 25 yards was spilt by Bishop, although the keeper got enough behind the attempt to divert it just off target.
Paul Lewis and Jake Carroll were introduced to proceedings after half time. United went close to grabbing the initiative in the early stages of the second half when Reggie Lambe's low cross skidded off the wet surface towards Osadebe, who was unable to shape his shot on target from a promising position eight yards out.
The 49 travelling supporters didn't have to wait much longer though, as Reggie Lambe nodded home on the end of Brown's pin point cross from the left hand side to earn the lead for United on 51 minutes.
However it was a short lived advantage as Shawn McCoulsky slid in to direct Harry Bunn's square cross against the inside of the post and into the U's net four minutes later.
McCoulsky and Southend made it two on 62 minutes and in similar fashion with Hendrie on this occasion attacking down the left, and delivering a fine cross onto the head of the Shrimpers striker who again made no mistake to score past Mitov.
The U's continued to contest well in the encounter but unfortunately for Joe Dunne's men their League One opponents were in no mood to relinquish their advantage.
Michael Klass rattled United's cross bar on 77 minutes, before substitute Isaac Hutchinson did register a third for the hosts when drilling a shot into the bottom corner from 18 yards just moments after being brought on by Southend Manager Chris Powell.
The U's kick off their Checkatrade Trophy campaign against fellow East Anglian rivals Southend United tonight – Kick Off 7:45pm!
Joe Dunne's men make the short trip down to south Essex to take on Chris Powell's Sky Bet League One outfit, as United get underway in Southern Group B of the competition.
Tickets for travelling U's fans will be available to purchase upon arrival at Root Hall tonight.