Victory at Wembley would see the Sky Blues reach the FA Cup final for the first time since the club famously lifted the trophy in 1987.
Ahead of the big match, lets take a look back at five memorable matches between the two clubs including City’s win en route to the FA Cup final and some Darren Huckerby magic at Highfield Road.
Mifsud Stuns Old Trafford
Though few football enthusiasts may know the name Michael Mifsud, the Maltese striker is revered as a hero in Coventry.
In the 2007–08 League Cup, City, who was then in the Championship, faced off against Sir Alex Ferguson’s victorious Manchester United squad in the third round.
While many anticipated a straightforward victory for the defending Premier League winners, Coventry and Mifsud had different plans.
On minute 27, the striker headed home Michael Doyle’s cross to break the tie and quiet the Old Trafford crowd.
And on minute 70, the Malta international finished clinically to complete a historic triumph and send the 11,000 travelling Sky Blues supporters into a frenzy.
Michael Carrick was used as a substitute for future World Cup and Champions League champion Gerard Pique and Portugal international Nani in United’s squad.
Hartson brace in vain for relegation-threatened Sky Blues
Coventry were in need of a miracle when they headed to Old Trafford in April 2001 with City embroiled in a relegation battle and United on course to win the Premier League title.
Buoyed by a 3-1 win at rivals Leicester City one week earlier, the Sky Blues took a shock lead when in-form striker John Hartson slid home a composed finish at the second attempt with the game 10 minutes old.
United turned the game on its head courtesy of a Dwight Yorke brace only for Hartson to level just past the half-hour mark in a frantic first half when he powered home a header at the back post.
Late goals from Ryan Giggs and Paul Scholes eventually sealed the points for United although Gordon Strachan’s City side showed plenty of spirit in defeat.
City would ultimately suffer relegation from the top flight at the end of the season, claiming just a single victory from their remaining five league matches.
The game is the last meeting between the two clubs in the Premier League.
Huckerby Magic Downs Champions United
On December 28, 1997, Coventry were staring down the barrel of a sixth league defeat in seven matches as they trailed Sir Alex Ferguson’s Manchester United 2-1 at Highfield Road with just four minutes remaining.
After Noel Whelan’s 12th-minute opener, Ole Gunnar Solskjaer and Teddy Sheringham struck either side of the break to complete an impressive turnaround from the defending Premier League champions.
However, a mazy run from Darren Huckerby drew a foul in the box which allowed former United man Dion Dublin to step up and coolly pick out the top left corner of the goal from the penalty spot.
And another moment of magic from Huckerby just two minutes later completed a stunning comeback.
Huckerby collected the ball just inside the United half and weaved his way past two defenders before sliding the ball into the bottom right corner.
Huckerby’s heroics ended United’s six-game winning run in the league and helped turn City’s fortunes around as the club enjoyed a fine second half of the season while the victory proved City’s only win against the Red Devils in the Premier League era.
Busst suffers career-ending injury
Many consider the career-ending injury suffered by Coventry’s David Busst at Old Trafford in April 1996 to be one of the worst in the history of the sport.
Busst unintentionally collided with United pair Dennis Irwin and Brian McClair just 87 seconds into the game and sustained compound fractures to the tibia and fibula in his right leg.
United goalkeeper Peter Schmeichel immediately threw the ball out of play for Busst to receive treatment and covered his face with his gloves such was the extent of the latter’s injury.
The game was stopped for nine minutes before Busst was carried off on a stretcher with blood from the wound cleaned off the pitch with water and sand.
Few remember Eric Cantona’s winning goal.
Despite having 22 operations, Busst never played a professional game again after contracting MRSA while in hospital which further damaged the tissue and muscle in his leg.
Busst is now the head of Sky Blues in the Community after taking up a non-playing role with the club following his forced early retirement.
Houchen the hero at frozen Old Trafford
Coventry City’s famous FA Cup triumph in 1987 is comfortably the greatest day in the club’s history.
However, en route to the final, the Sky Blues overcame Sir Alex Ferguson’s Manchester United in a fourth round tie at Old Trafford.
Ferguson replaced Ron Atkinson in the United dugout earlier that season with Coventry also proving to be the latter’s last league opponents as Red Devils boss.
After United’s electric undersoil heating failed to cope with overnight temperatures of minus seven degrees Celsius, half of the pitch was frozen and covered by frost.
But that did little to deter the Sky Blues as Keith Houchen bundled home the game’s only goal on 20 minutes, the first of five he scored in that season’s competition.
Further wins against Stoke City, Sheffield Wednesday and Leeds United sent City into their first FA Cup final and the rest, as they say, is history.
The victory against United remains Coventry’s only success against the Red Devils in the FA Cup to date.
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