Coventry 3-2 Tottenham (FA Cup Final)
Date Played: 16th May 1987
The match started off at a frantic pace and just after two minutes, Chris waddle picked up a clearance on the right and crossed near the post. Clive Allen firmly headed the ball past Steve Ogrizovic to put Spurs 1-0 in front. Only minutes later, Dave Bennet went round Ray Clemence and tucked the ball into an empty net to level the proceedings. With few minutes of the first half remaining, Glenn Hoddle took a free kick finding Richard Gough who flicked the ball into the goalmouth. Both Mabbutt and Kilcline went for the ball together and it went into a gaping net. Twenty minutes into the second half, Houchens diving header provided Coventry with an equalizer. With the scores now level, Coventry now started to pile on all the pressure and Clemence had to make a string of fine saves and make the game go into extra time. Seven minutes into extra time, Lloyd McGrath crossed the ball towards the Spurs goal from outside the area. Mabbutt tried to intercept, however the ball hit his left knee and flew over Ray Clemences head to make it 3-2.

Coventry 5-4 Nottingham Forest
Date Played – 28th November 1990
This league cup thriller is arguably the greatest ever match played in the league cup, despite only being a fourth round tie. After only a quarter of an hour, a corner from Mickey Glyn on the left was nodded onto David Speedie, whose powerful header was blocked on the line by Steve Hodge, however Kevin Gallacher hammered home the rebound from point blank range. Only a minute later Gallacher doubled his and Coventry’s goal tally to two. Coventry continued to dominate the match and on the half hour mark a long Coventry clearance was headed on by Steve Livingstone towards Kevin Gallacher who scored his third and Covetry’s third of the match. Coventry continued to play magnificently well and Gallagher was in sparkling form. With five minutes before the end of the half Coventry’s Peter Billing headed the ball forward and Gallacher volleyed through the legs of Brian Laws. Nigel Clough scored one minute later to make it 4-1 and with two minutes left of the half, Steve Hodge assisted the ball to Nigel Clough who scored to make it 4-2. And during injury time of the first half, the comeback was looking really likely as Gary Crosby passed to Nigel Clough who scored an amazing five minute hat trick and now the match was amazingly 4-3 by half time. With ten minutes into the second half, Gary parker leveled the score line with a low strike and it was 4-4. The match amazingly continued at the same pace as an overhead free kick by Cyril Regis was blocked on the line by Laws and Livingstone pounced to head home the rebound from close range and seal the match for Coventry 5-4.

Coventry City 2-2 Derby County
Date Played – 4th December 2004
In what proved to be a thrilling encounter between the two teams, Derby County stormed back from coming two behind, however Coventry grabbed a vital away point. Stephen Highes gave the sky blues the lead after 21 minutes when he smashed a low shot in to the back of the net. City were beginning to play some fine football as Gary McSheffrey nearly made it 2-0 to the sky blues. Late on in the second half, dale Adebola made the score line 2-0 as Coventry were looking at an away win, however the match ended incredibly. Derby scored two goals in the last two minutes of the match through, Gregorz Rasiak and Paul Peschisolido to finish the score line 2-2.