Both sides booked their tickets to the final four thanks to astounding quarter-final successes, as Mark Robins's Championship battlers bested Wolverhampton Wanderers 3-2 at Molineux.
Meanwhile, the Red Devils - who have won the FA Cup on 12 occasions - were 4-3 extra-time victors over Liverpool at Old Trafford, and either Manchester City or Chelsea will be waiting for the victor in the final.
Here, Sports Mole takes an in-depth look at the head-to-head record and previous meetings between the two sides.
Head-to-head record
Previous meetings: 83
Coventry wins: 23
Draws: 17
Man Utd wins: 43
Formerly familiar foes during Coventry's days in the Premier League, which came to an end in 2001 and have not returned since, the 83rd and most recent meeting between the Sky Blues and Man United came in the 2007-08 League Cup.
Then under the tutelage of Iain Dowie, Coventry travelled to Old Trafford for a third-round clash with Alex Ferguson's side, but the Red Devils were far from full strength, fielding forgotten names such as Chris Eagles, Phil Bardsley and Dong Fangzhuo.
Jonny Evans - who is expected to miss the semi-final due to injury - also started for Man United on that day, but it was an occasion to forget for Ferguson's young squad, as two strikes from Michael Mifsud propelled Coventry to a momentous 2-0 triumph.
Before teaching the fledgling Red Devils a footballing lesson on that day, though, Coventry lost six Premier League games in a row against Man United from 1998 to 2001 and only won one of their top-flight meetings after the Premier League's inception in 1992.
That sole success was a 3-2 triumph at Highfield Road in December 1997, where Dion Dublin was among the Coventry scorers, but FA Cup meetings have been few and far between down the years with just six in total.
However, the most recent of those clashes came in the 1986-87 season, where Coventry prevailed 1-0 in the fourth round before going on to lift their first and only FA Cup to date, but Man United had earned a 2-1 fourth-round win two years prior en route to glory.
The Red Devils have eliminated Coventry from the FA Cup in four of their previous five showdowns, although they needed a replay to get the job done in the 1912-13 first round, and their overall record against the Sky Blues stands at 43 wins from 83 matches.
Meanwhile, Coventry have 23 triumphs under their belt from this fixture, in which there have also been 17 draws, but something must give in Sunday's intriguing battle between the two old foes.
Last 20 meetings
Sep 26, 2007: Man Utd 0-2 Coventry (League Cup Third Round)
Apr 14, 2001: Man Utd 4-2 Coventry (Premier League)
Nov 04, 2000: Coventry 1-2 Man Utd (Premier League)
Feb 05, 2000: Man Utd 3-2 Coventry (Premier League)
Aug 25, 1999: Coventry 1-2 Man Utd (Premier League)
Feb 20, 1999: Coventry 0-1 Man Utd (Premier League)
Sep 12, 1998: Man Utd 2-0 Coventry (Premier League)
Dec 28, 1997: Coventry 3-2 Man Utd (Premier League)
Aug 30, 1997: Man Utd 3-0 Coventry (Premier League)
Mar 01, 1997: Man Utd 3-1 Coventry (Premier League)
Jan 18, 1997: Coventry 0-2 Man Utd (Premier League)
Apr 08, 1996: Man Utd 1-0 Coventry (Premier League)
Nov 22, 1995: Coventry 0-4 Man Utd (Premier League)
May 01, 1995: Coventry 2-3 Man Utd (Premier League)
Jan 03, 1995: Man Utd 2-0 Coventry (Premier League)
May 08, 1994: Man Utd 0-0 Coventry (Premier League)
Nov 27, 1993: Coventry 0-1 Man Utd (Premier League)
Apr 12, 1993: Coventry 0-1 Man Utd (Premier League)
Dec 28, 1992: Man Utd 5-0 Coventry (Premier League)
Feb 29, 1992: Coventry 0-0 Man Utd (First Division)
Previous FA Cup meetings
Jan 31, 1987: Man Utd 0-1 Coventry (Fourth Round)
Jan 26, 1985: Man Utd 2-1 Coventry (Fourth Round)
Mar 30, 1963: Coventry 1-3 Man Utd (Quarter-finals)
Jan 16, 1913: Coventry 1-2 Man Utd (First Round replay)
Jan 11, 1913: Man Utd 1-1 Coventry (First Round)
Feb 03, 1912: Coventry 1-5 Man Utd (Second Round)
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