DISAPPOINTMENT was plastered all over Tom Webb's face as the Tigers' talisman came to terms with yet another Gloucester City hard luck story.
The battling Tigers didn't deserve what happened to them in the final three minutes of Wednesday night's Whaddon Road clash – to lose 2-0 was nothing short of a scandal.
They may not have peppered the Orient goal or battered their way in to the lead at any point but for battling spirit alone Dave Mehew's men deserved at least a replay.
But after Dave Mooney flicked a header past the despairing hand of Mike Green on 87 minutes to give the Londoners the lead, City had run their race.
Dean Cox's second goal a minute later was unduly harsh as was the taunting celebration in front of the City support, but by then it didn't really matter.
Disconsolate after the final whistle, City's record appearance maker was able to say that game number 504 will go down in memory as the best night he can remember in yellow and black.
"It's a pretty cruel way to lose," Webb said, "I don't think they really had any attempts on goal in the second half before they scored.
"The problem was that we didn't get that early goal because for the first 15-20 minutes we were in the ascendancy and if we had have got the goal it would have been a different story.
"It was brilliant to have so many fans in the ground supporting us, it was the best game of football that I have ever been involved with.
"It was a great atmosphere right from the warm-up and it felt like a proper League game.
"It felt really special, I am just bitterly disappointed that the result went the wrong way.
"We had a right old go at them early in the game. We said that at one stage in the game that we would have a spell where we were on top, unfortunately we didn't get the crucial goal."
That start saw City fly out of the blocks at a searing and impressive pace.
Just a minute had passed when Tom Hamblin headed Lewis Hogg's corner towards goal and Darren Edwards' scuffed shot was desperately cleared by Orient midfielder Jimmy Smith.
Jack Harris was next to test the O's, cutting out an errant ball on halfway and driving at the heart of the visitors' defence, but he dragged a shot wide with a rampaging Mitch Harding well placed.
City's superb start almost reaped benefit on 12 minutes as Jordan Goddard skilfully wriggled free in the box and fell under a clumsy challenge but referee Steve Rushton ignored the vehement protests for a penalty.
After being a virtual spectator for 40 minutes, City keeper Mike Green was pressed into action for the first time when Cox wriggled free to send a shot arrowing towards the corner of the net.
Ryan Brunt's deflected effort rebounded against the frame of the goal after Cox had been allowed to cross from the right, while Green somehow got hands to deflect Mooney's dipping 35-yard volley round the post.
The late flurry of action in the first half was recreated at the end of the second period too, but not before City held firm against an increasing tide of Orient pressure.
But for all their possession and patience, the League One side had not had a shot on Green's goal until an error from Chris Holland gifted Lloyd James the opportunity to cross from the right and Mooney did the rest with a glancing header.
Worse was to follow right from the kick-off as a clearly-deflated City side conceded another goal.
Skipper Matt Coupe got his feet in a tangle and Cox, Orient's liveliest player throughout, was allowed a clear run on goal to stroke home a second.
Green saved again from Mooney to deny Orient an even more flattering scoreline, but by then the City players were on their knees, a spent force having given so much for the cause.
But Webb knows that the disappointment cannot be allowed to last, not when there's a crucial Blue Square Bet North clash with Chester FC to contend with on Sunday.
"It's been a 23-year wait to get into the first round of the cup and we performed well, the important thing is that we all take some of what happened in to the league," he said.
"If we start at that tempo against Sunday at Chester then I am sure we can improve our league form."
Gloucester City: MJ Green, T Hamblin, M Coupe, C Holland; MF Green (J Tillson 88), T Webb, L Hogg, J Goddard (S Davies 60), J Harris; M Harding (W Morford 55), D Edwards.
Subs not used: M Liddiard, S Rawlings, A Mann, N Mustoe.
Leyton Orient: R Allsop; M Odubajo (L McSweeney 58), N Clarke, M Baudry, G Sawyer; J Smith (M Rowlands 87), L James, A Griffith, D Cox; R Brunt (K Lisbie (61) , D Mooney.
Subs not used: J Jones, B Chorley, M Symes, L Cook.
Referee: S Rushton
Att: 1,381 (163 away)
Star Man: MIke Green (goalkeeper)