Crawley Town are bottom of their group after suffering a 3-1 defeat away to Portsmouth in the Checkatrade Trophy.
The result follows their 2-0 defeat at home to Charlton in August and means with one more game still to play against Fulham under-23s on November 7, they cannot progress into the knock-out stages.
Portsmouth took a 2-0 lead into half-time following two goals in four minutes around the half hour mark by Matt Clarke and Oliver Hawkins.
Reds fought themselves back into the game through a 64th minute goal by Dutch midfielder Moussa Sanoh, his first for the club.
But the contest was put to bed just six minutes later with a third goal by Pompey’s Stuart O’Keefe.
Harry Kewell made eight changes to the side which lost to Carlisle on Saturday with Yusuf Mersin putting on the keeper’s gloves, while Aryan Tajbakhsh, Joe McNerney, Kaby Djalo, Panutche Camara, Moussa Sanoh, Ibrahim Meite and Billy Clifford all started.
They replaced Glenn Morris, Lewis Young, Mark Connolly, Enzio Boldewijn, Jimmy Smith, Jordan Roberts, Josh Lelan and Cedric Evina.
Dennon Lewis returned from injury which has seen him miss four games and was on the bench.
However there was no place in the squad for Dean Cox, who was ill.
Portsmouth made six changes to the side which lost to Oldham Athletic in League 1 on Saturday.
Both teams started brightly in attacking mode with Crawley’s Meite having the first chance who pounced on a loose ball and passed to Clifford whose shot went straight to keeper Luke McGee.
After some early Reds possession, Portsmouth’s Curtis Main had a shot went narrowly wide of goal from the left hand side.
Djalo looked good in his first game since August and had a long-range effort saved after 20 minutes as Crawley went on the attack.
However Portsmouth took the lead on 30 minutes when an initial attempt by Main was well-saved by Mersin but fell to Clarke for a good finish.
Pompey made it 2-0 five minutes later when shot bounced out for Hawkins to score from close-range.
Just before half-time Reds were looking to pull a goal back as the Meite looked dangerous run and had a shot blocked by a defender.
Payne narrowly missed scoring from a well-taken free-kick from 25 yards just before the break.
Crawley made a good start to the second half with two corners. Meite was not able to control a pass by Clifford and the ball rolled out for a goalkick.
Djalo received a yellow card on 52nd minute for a challenge.
Portsmouth made a double substitution after 62 minutes with Brandon Haunstrop and Jamal Lowe coming on for Adam May and Danny Rose.
A penalty appeal by Sanoh was turned down but he soon was in the thick of the action again.
Sanoh then scored in the 65th minute from a through-ball which he slipped under the keeper from inside the box to score his first goal for the club.
Portsmouth sealed victory after 71 minutes when O’Keefe placed into an empty net from the edge of the area from a cut-back by Bennett.
Boldewijn and Lewis came on for Tajbakhsh and Camara with 15 minutes to go.
In the final stages Portsmouth’s Kyle Bennett missed a free-header which flew wide as the final minutes ran down before the final whistle.
REDS: Mersin, Tajbakhsh (Lewis 75), Yorwerth, McNerney, Djalo (Smith 87), Bulman (capt), Payne, Camara (Boldwewijn 75), Clifford, Sanoh, Meite
Unused subs: Morris, Connolly, Lelan, Evina
PORTSMOUTH: McGee, Evans (capt), Hawkins, Clarke, Donohue, Rose (Lowe 62), May (Haunstrup 62), O’Keefe (Close 87), Naismith, Bennett, Main
Unused subs: Bass, Talbot, Kennedy, Chaplin
ATTENDANCE: 1,527 (44 away)