Next Saturday the Sky Blues face Premiership opposition in the fourth round of the FA Cup with City travelling to face their old rivals Southampton (they have played Saints more than any other club in Football League games) and the game offers a chance to reverse Coventry's poor Cup record against the South Coast team.
In 1912 City won an FA Cup tie at the Dell, Southampton's former ground, when both clubs were in the old Southern League but since then the Saints have progressed on all three occasions that the club have been drawn together in the competition despite Coventry being drawn first out of the hat each time.
City and the Saints met in the first Round which was the equivalent of the modern third round in 1912. As Southern League clubs they were classed as non-league clubs when in fact there were only two Football League divisions and Southern League was like a Third Division. Coventry had earned a reputation as Cup giantkillers two years earlier by defeating two First Division clubs in reaching the quarter finals as a non-league club. They had already done the league double over the South Coast team. Contemporary match reports say that the Coventry fans 'numbered about a couple of hundred and were lavishly decorated with blue ribbons'. City scored two early goals from Harry Parkes and Fred 'Boxer' Turnbull and managed to survive a lot of pressure from the home team to win 2-0 with their Welsh international goalkeeper Bob Evans pulling off several good saves. City were drawn at home against First Division Manchester United in the second round and lost 5-1 in front of an almost capacity 17,000 gate.
The next FA Cup meeting was in the first round of 1959-60 when both clubs were in the top six of Division Three and City were drawn as the home side. Ray Straw put City ahead in the 16th minute but Derek Reeves equalised on 64 minutes to force a replay in front of 14,000. Three weeks earlier City had lost a league encounter at the Dell 5-1 and the Saints repeated that scoreline in the replay. An early John Page penalty was followed by two Terry Simpson goals in three minutes before half-time. Alan 'Digger' Daley pulled one back for the Bantams but further scores from George O'Brien and Terry Paine completed the scoring.
City were again first out of the fourth round hat in 1990-91 having defeated Wigan Athletic in a replay in the third round. Terry Butcher had taken over as manager and was changing the personnel but still fielded five of the '87 Wembley team as well as Brian Borrows. Butcher omitted David Speedie and the feisty Scot looked to be heading for the Highfield Road exit. Brian Kilcline gave City the lead just before half-time but Alan Shearer equalised five minutes after the break and take the tie back to the Dell. An injury hit and flaccid City lost the replay 2-0 with Jimmy Case and Rod Wallace scoring in front of 17,000 on a bitterly cold night.
The last time the clubs were drawn together in the competition was in 2012 when the third round draw gave City the home advantage. When the tie took place on the first Saturday of January the Saints were top of the Championship whilst the Sky Blues were bottom and heading towards relegation. Southampton had already won the league game at the Ricoh, 4-2 in November. Gary McSheffrey gave City a fifth minute lead but James Ward-Prowse (17 years old at the time) equalised and future City defender Aaron Martin headed the winner eight minutes from time. In addition to Martin three other Saints' players had links to City; Jack Cork and Danny Fox started and Jack Stephens, a future loanee, came on as a substitute. A miserable 9,000 crowd watched the tie.
The tie with Southampton is the 13th time the Sky Blues have been drawn against Premiership opposition since the club was relegated in 2001. On the previous nine occasions City have progressed just three times, against Blackburn twice (2008 and 2009) and against Stoke City (2018). The other Premiership clubs that they have failed to beat are: Tottenham (2002 and 2013), Newcastle (2005), Middlesbrough (2006), Chelsea (2009), Portsmouth (2010), Birmingham (2011), Arsenal (2014) and Brighton (2018).
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