Sky Blues leave the Matchroom Stadium empty handed after goals from Orient's Dean Cox and David Mooney
Coventry City left the Matchroom Stadium empty handed for the third time this season after they went down 2-0 to Leyton Orient.
Second half goals from Dean Cox and substitute David Mooney proved enough for Russell Slade's side on a wet night in the capital which saw Sky Blues boss Steven Pressley hand a full senior debut to 16-year-old George Thomas in place of the injured Leon Clarke.
The change was the only one from the side that travelled to Arsenal the previous Friday night, and the occasion did not seem to faze the youngster either as he showed some neat and confident touches to retain possession for the Sky Blues in the opening stages.
It was the home side who registered the first effort of the night on goal though after nine minutes when Moses Odubajo played a lateral ball to Cox who shot at goal and forced a low save out of Joe Murphy.
The resulting corner delivery also seemed to cause a slight bit of panic in City's six yard box although Billy Daniels was on hand to clear the danger.
The Sky Blues registered their own first effort on target four minutes later though when Carl Baker's speculative effort from just over 20 yards saw Eldin Jakupovic make a comfortable save.
Jakupovic was then very nearly left red faced when his kick was charged down by Franck Moussa after quarter of an hour, the Orient 'keeper relieved to see the ball go behind for a goal kick.
City went close again after 22 minutes when a quick break saw Billy Daniels with the ball on the edge of the area, the midfielder hitting a half volley which went just wide of the foot of the far post.
Moments later though Orient were a whisker away from the opener when Cox was picked out again, this time by Chris Dagnall although the wideman could only find the side netting from ten yards.
The hosts should have been ahead on the half hour though when Odubajo got down the right flank and squared a ball to the unmarked Dagnall who, from 12 yards out, hit a first time shot which flew high over the bar.
On balance it was Orient that saw out the half the more likely of the two sides to score which Odubajo, Vincelot and Kebvin Lisbie all registering efforts on target but none that gave Murphy any problems in City's goal.
Lisbie went closer four minutes after the restart though when a looping ball from Vincelot picked out the striker who only had Murphy to beat but the City 'keeper stood up well to make the stop.
Jakupovic was forced into making his first real save of the game after 53 minutes though when Moussa took the ball around three players before shooting from just inside the area, the shot taking a slight deflection which nearly took it beyond the reach of the Orient 'keeper who was at full stretch to deny City an opener.
Orient looked like they would take the lead a minute later though when Dagnall went down in the area under pressure from Andy Webster, leaving referee Michael Bull to point to the spot.
Lisbie stepped up to take the penalty and it was a good one, low and at the far corner, but Murphy pulled out a stunning one handed save to deny him.
City's joy was shortlived though as the resulting throw in was sent deep into the Sky Blues area and got a glancing head before reaching Dean Cox who swept the ball home.
The Sky Blues showed no signs of defeatism though and nearly grabbed a leveller a minute after the hour when Baker's cheeky free kick from 20 yards saw him bend a low shot around the outside of the wall and nearly beat Jakupovic at his near post, the Orient 'keeper having to get down smartly.
The home side went a whisker away from a second three minutes later though when Lloyd James lashed a shot across the face of goal which went just wide of the far post.
City substitute Denzel Slager forced a save out of Jakupovic after 72 minutes with an effort from an acute angle which the Orient shot stopper palmed away for a corner.
He was forced to do the same but in more acrobatic fashion a minute later when Carl Baker battled his way to the edge of the area and unleashed a shot destined for the top corner until the Jakupovic pushed it around his post.
Orient got a second with nine minutes of the game to go and it was a harsh one for Joe Murphy to concede. David Mooney had been on the pitch for five minutes when he hit a 30-yard effort that moved around in the wind and deceived Murphy who got a hand to the shot but could not stop it going in.
Attendance: 5,077 (641 Sky Blue Army)
Coventry City: Murphy (GK), Adams, Webster, Seaborne, Christie, Daniels (Slager 61), C Thomas, Fleck, Baker (c), Moussa (Barton 86), G Thomas (J Clarke 45)
Subs: Burge (GK), Willis, Phillips, Haynes
LeytonOrient: Jakupovic, Omozusi, Vincelot, Cuthbert (Sawyer 88), Baudry, Cox (Ness 74), James, Lisbie (Mooney 76), Odubajo, N Clarke (c), Dagnall
Subs: Larkins (GK), Bartley, Loza, Simpson