It was a night of missed chances for the Sky Blues at a packed Ricoh Arena as they left themselves with a mammoth task in order to reach Wembley after a 3-0 Johnstone's Paint Trophy Area Final first-leg defeat to Crewe Alexandra.
The 30,000 City fans could have been forgiven for losing count of the number of chances the home side as they were denied by the woodwork and a series of top class saves from Alex 'keeper Steve Phillips and then were undone by a second half brace from Bradden Inman and a third from AJ Leitch-Smith to cap off a disappointing night.
City boss Robins opted to stick with the same starting line-up that picked up three points at Bramall Lane the previous weekend and they were treated to a walk-out infront of a sell-out crowd at the Ricoh Arena.
The fans did their job to ramp up the atmosphere as the game kicked off but while the intensity on the pitch matched the noise, there was little in the way of chances until the 16th minute when Carl Baker got round Mark Ellis down the righ flank and cut a ball back for Leon Clarke whose first-time effort went just the wrong side of Steve Phillips' near post.
The chance spurred the Sky Blues on as they went on to dominate the next five minutes, camped out in Crewe's half. Cyrus Christie did superbly down the right to beat three players and win a corner and Chuks Aneke nearly put his headed clearance into the back of his own net at the back post under pressure from Clarke.
Clarke had another chance on 22 minutes after a somewhat scrappy exchange in the Alex box when Baker swung in a corner delivery that caused chaos in the six-yard as the ball bobbled around, eventually falling to Clarke who scooped an effort aimed inside the far post that Phillips did well to get down and keep out.
Franck Moussa was next three minutes later when Baker sparked a swift counter attack which saw the ball spread wide to Moussa to shoot from 20 yards, Phillips making another strong save.
Fans were then left with their heads in their hands in disbelief on 29 minutes when Phillips pulled off a stunning save to deny Stephen Elliott ten yards out although the danger was not over as Gary McSheffrey picked up the loose ball and played it across the face of goal, Adam Dugdale toe-poking a clearance as far as Steve Jennings on the edge of the area whose first time shot whistled just past the post.
Crewe registered their first effort of the night four minutes after the half hour, albeit off target, as Baker's midfield pass was dispossessed, allowing the visitors to break with AJ Leitch-Smith floating a cross in for the unmarked Abdul Osman who directed his header wide despite having plenty of time to place it.
City went a whisker away from an opener again with a minute of the first half to go when Baker continued to terrorize the back four down the right and cut back another dangerous ball which was cleared behind.
McSheffrey's resulting corner delivery caused more panic as it flashed across the six-yard box, taking a touch off Ellis for another corner.
City went even closer with the next corner as McSheffrey again delivered a dangerous ball which found Clarke at the back posyt to fashion an overhead kick which went inches wide.
The Sky Blues then finished the half on a strong note as they broke away with Baker feeding Jennings who went one-on-one with Phillips but put his finish just over the bar.
They carried their momentum through into the second half and forced another outstanding save out of Phillips when Elliott poked an effort that was bound for the far corner until the 'keeper tipped it away.
It was the visitors that took the lead though against the run of play when Aneke squared a ball across the edge of the area for Inman who took two touches before firing past Dunn into the top corner.
The Sky Blues were desperately unlucky not to score again just two minutes after going behind when Elliott's personal battle with Phillipsm continued, the 'keeper again thwarting Elliott's afforts to level with another reaction stop.
City's rotten luck in front of goal continued on the hour when Clarke was sent racing down the left and fired in a low cross which took a bounce off Ellis and then ricocheted off Bakwer just two yards in front of him, the ball looking destined for the bottom corner until Phillips again tipped the ball away.
Three minutes later it was the post that came to Phillips' rescue as Baker was layed on with a ball that he struck sweetly from 15 yards only to see the ball smash off the post. City kept up the pressure though and heads were again left in hands when Blair Adams low, fizzing ball across the six-yard area missed the ties of both Elliott and Clarke by inches.
The opener infact only seemed to spur both the Sky Blues and their 29,000-strong support and they continued to pelt the Crewe area with deliveries and cut the back line open with short, sharp passes only to be frustrated by some determined defending.
Crewe's apparent game plan of sitting back and hitting City on the break bore fruit once again though with 13 minutes to go as Inman this time went alone.
The striker took the ball midway inside City's half and danced his way through the Sky Blues back four before firing past Dunn and into the bottom corner.
City had it all to do as the game entered the last ten minutes, a period they started with a McSheffrey free kick that sailed just over the bar from 20 yards.
The game was put beyond City's reach with six minutes to go though when a ball spread to Leitch-Smith allowed the striker to cut inside William Edjenguele and thread a pinpoint finish beyond Dunn and into the far bottom corner.
The Sky Blues continued to press forward in attempt to grab a goal to take with them into the second leg and they nearly got it on 86 minutes when a floated ball from substitute James Bailey picked out Clarke to head just wide of the far post.
Crewe went straight up the other end though and forced an excellent save out of Dunn who palmed over a shot from Aneke.
City never gave up as referee Graham Salisbury signalled five minutes of added time but although the Sky Blues could not be accused of a lack of endeavour the game ended without them being able to take a goal to the Alexandra Stadium in two weeks time.
Attendance: 31,054 (1,472 away)
Coventry City: Murphy (Dunn 45), Christie, Edjenguele, Wood, Adams, Jennings, Baker (c), Moussa, McSheffrey (Bailey 81), Elliott (Ball 73), L Clarke
Subs: Dunn (GK), J Clarke, Thomas
Crewe Alexandra: Phillips, Tootle, Ellis, Dugdale, Murphy (c), Leitch-Smith, Moore, Mellor, Osman, Aneke, Inman (Robertson 81)
Subs: Martin (GK), Clayton, Turton, Colclough
Referee: G Salisbury
Assistant Referees: D Richardson, A Tankard
Fourth Official: J Adcock