Orient were cruelly denied their place in the third round of the Capital One Cup as an extra-time goal from Robbie Brady was enough to send Premier League side Hull City through.
Having been the better side for much for the 120 minutes Orient will feel hard done by as Brady pounced just one minute after coming on in extra-time to swivel and fire past Jamie Jones in the Orient goal.
The Tigers made 11 changes from the side that played on Saturday against Norwich whilst Russell Slade dropped Mathieu Baudry to the bench and brought Marvin Bartley in for his first start.
Orient began the first half on top and their dominance remained for most of the first period.
An early corner saw Lloyd James cross the ball in from the right and Romain Vincelot escape his marker to unleash a volley narrowly over the bar.
What followed was a strong spell of possession for the O’s though neither goalkeeper was made to work inside the first 20 minutes.
With 28 minutes gone Orient started to find their attacking rhythm and almost snatched the lead on the break when Vincelot broke through midfield and fed Dean Cox who slipped it to the in-form David Mooney but his shot from distance flew over the bar.
It was that Mooney in the thick of it again 10 minutes later when Kevin Lisbie held the ball up on the right and laid it into the path of Cox who swung in a deep cross for the Irishman to leap clear of Alex Bruce but his header bounced narrowly wide of the target.
Jones was a spectator for much of the first period as Orient held their shape and prevented any City openings as Russell Slade would have entered the half-time interval much the happier of the two managers.
It was not until a minute after the restart that the Premier League side had their first chance of note when a Cameron Stewart corner was met by the head of David Meyler but the impressive Elliot Omozusi was on hand to scramble the ball off of the line to safety.
Hull boss Steve Bruce had obviously had words with his players who raised the tempo for the start of the second period and had the best of the opening exchanges though Orient remained resilient and appeared to weather the early storm.
Having started the season in fine form on the right of midfield, Moses Odubajo looked equally at home in the right-back birth and found himself in a great position just before the hour mark but could only slice Mooney’s cross wide
Orient used the opening to build a platform for a good spell and after the visitors had controlled the early stages of the second half, Orient began to find their rhythm after the hour mark when Mooney and Cox both had efforts following good moves though neither really tested Harper.
The O’s best chance would come on 75 minutes when substitute Yohann Lasimant robbed the ball off of Alex Bruce and hurtled towards the Tigers goal, however deciding to take the shot on early, his effort sliced wide off the outside of his boot and he would have been disappointed not to have found the target.
Orient looked dangerous from set-plays throughout and the impressive Vincelot came close again to his first of the season when he headed down a James corner which was blocked and then scrambled another effort towards goal that was blocked on the line by Bruce.
The visitors made a late charge and twice Jones was called upon to save well from Matty Fryatt who looked the most likely to break the deficit for Steve Bruce’s side.
With 90 minutes up and the score still locked at 0-0 the tie went to extra-time, the second time within a year that this happened when the two clubs have faced each other following the FA Cup third round tie last season.
As to be expected, extra-time was a more turgid affair as both sides struggled to maintain the intensity of the opening 90 minutes and but for some feisty tackles, the first half of extra-time produced little action of note.
Instead the turning point came within a minute of the restart when Nathan Clarke initially did brilliantly to block a cross from the right but then struggled to clear the danger as Brady pounced to fire home from eight yards leaving Jones with no chance.
Neither teams managed to finish in the last few minutes despite efforts from both sides, it resulted in a further 30 minutes of extra time.
Hull were content to run the clock down for the remainder and though the O’s forced some pressure with a series of long throws, it was the Tigers who would finish victorious though Slade and his side could take pride in their performance and comfort from the O’s fans who gave them a standing ovation on the final whistle in recognition of their effort and endeavor.
ORIENT: Jones, Omozusi, Vincelot, Cuthbert, Cox, James, Lisbie (Lasmiant 66) , Mooney, Odubajo, Clarke (c ), Bartley (69 Gorman). Subs not used: Baudry, Larkins (gk ), Lee, Vanderhyde.
HULL: Harper, Rosenior, Bruce, Meylor, Fryatt, McShane ( c), Boyd, Dudgeon, McLean (Brady 115), Stewart (Townsend 55), Proschwitz (Jahraldo-Martin 67). Subs not used: Jakupovic (gk), Chester, Davies, Aluko.
GOAL: 106 Brady.
BOOKINGS: Townsend 92, Martin 94.
REFEREE: Gavin Ward
ATTENDANCE: 3181 (384)