Hosting Tottenham Hotspur at the CBS Arena, Mark Robins’ side just past the hour-mark, through summer signing Brandon Thomas-Asante’s second goal for the club.
However, the visitors equalised with just two minutes of normal time remaining thanks to Djed Spence, before Brennan Johnson’s injury time strike sent the Premier League side through.
That will have left Coventry crestfallen at having nothing to show for their efforts, although it will not just be the result that will leave the Sky Blues disappointed about that match.
Sky Blues facing another injury concern
One seemingly big moment for the hosts during Wednesday night’s game came with around 20 minutes of normal time remaining.
That moment saw Ben Sheaf come off the bench, to replace Josh Eccles for just his second appearance of the campaign, amid a string of injury issues.
However, it seems as though the 26-year-old’s latest return to action could yet turn out to be a rather short-lived one.
Speaking after the game, Robins revealed that the midfielder had to have ice on his ankle in the dressing room post-match, and that he does not yet know how serious the setback is.
Given his sizable influence in the centre of the park, that latest blow for Sheaf will undoubtedly be a concern for Coventry going forward.
It could arguably, also cause some frustration for the club when looking back on one potential signing they missed out on during this summer’s transfer window.
Coventry missed out on potential Ben Sheaf cover
By the time the transfer market closed on the 30th August, the Sky Blues had completed the signings of six new first-team players.
However, it appears they did not get deals done for every player they were looking at, and one of those they were unable to secure the services of, was Marko Stamenic.
Back in June, Red Star Belgrade manager Nenad Milijas had claimed that the midfielder had agreed a deal to complete a permanent move to Coventry.
Ultimately though, no such deal would materialise, and instead, Stamenic would join Premier League side Nottingham Forest shortly after, before immediately being loaned to Olympiacos.
As a result, Coventry missed out on a signing that, amid these latest fitness concerns around Sheaf, would have been rather useful.
With Stamenic primarily a holding midfielder, his signing would give the Sky Blues the depth they need in that area to cope with the absence of Sheaf.