Coventry's 2-0 defeat to Doncaster Rovers on Saturday brought to an end any aspirations of a Play-Off place in Sky Bet League 1 and a long-awaited top-six finish.
The last time the Sky Blues supporters were able to celebrate such a feat was at the end of the 1969/1970 season when Coventry finished sixth in the old First Division, then under the management of Noel Cantwell.
Since then the club's best finish has been seventh, once in 1977/78 and the other in 1988/89.
City were inaugural members of the Premier League, formed in 1992, however they were relegated to the old First Division in 2001 and then again to Sky Bet League 1 in 2011.
Earlier this season it looked as though they were on course to not just achieve a top-six place, but also promotion back to the Championship.
Tony Mowbray's side were top as recently as 24th November, but with just six wins to their name since then they have fallen to 12th which would still be the club's highest finish since 2006.
Following Saturday's defeat at the Keepmoat Stadium, manager Mowbray said: "That's the most disappointed I’ve been all year.
"We didn’t show enough fight, which is very disappointing for me. If you're a boxer in a boxing ring and you get punched in the nose, you have to fight back, and we didn't do that.
"There was a distinct lack of fight, and unfortunately I think it's the team we have got. I thought we would have to defend well against a team that would be on the front foot, pressing high up, and we couldn't do that.”
Where they've finished...
1970/71: 10th (First Division)
1971/72: 18th (First Division)
1972/73: 19th (First Division)
1973/74: 16th (First Division)
1974/75: 14th (First Division)
1975/76: 14th (First Division)
1976/77: 19th (First Division)
1977/78: 7th (First Division)
1978/79: 10th (First Division)
1979/80: 15th (First Division)
1980/81: 16th (First Division)
1981/82: 14th (First Division)
1982/83: 19th (First Division)
1983/84: 19th (First Division)
1984/85: 18th (First Division)
1985/86: 17th (First Division)
1986/87: 10th (First Division) - FA Cup Winners
1987/88: 10th (First Division)
1988/89: 7th (First Division)
1989/90: 12th (First Division)
1990/91: 16th (First Division)
1991/92: 19th (First Division)
1992/93: 15th (Premier League)
1993/94: 11th (Premier League)
1994/95: 16th (Premier League)
1995/96: 16th (Premier League)
1996/97: 17th (Premier League)
1997/98: 11th (Premier League)
1998/99: 15th (Premier League)
1999/00: 14th (Premier League)
2000/01: 19th (Premier League) - Relegated
2001/02: 11th (First Division)
2002/03: 20th (First Division)
2003/04: 12th (First Division)
2004/05: 19th (First Division)
2005/06: 8th (First Division)
2006/07: 17th (Championship)
2007/08: 21st (Championship)
2008/09: 17th (Championship)
2009/10: 19th (Championship)
2010/11: 18th (Championship)
2011/12: 23rd (Championship) - Relegated
2012/13: 15th (League 1)
2013/14: 18th (League 1)
2014/15: 17th (League 1)