We take a look back at some of those players to have played for both the Sky Blues and Birmingham City ahead of Friday night's clash...
Republic of Ireland international central defender Gary Breen joined Birmingham City in 1996 after plying his trade in the lower reaches of the Football League.
He joined for £250,000 and impressed during his solitary season in the First Division and Premier League Coventry City came calling, for whom he joined for £2.5 million the following summer.
Breen played five full seasons for the Sky Blues, four of those in the Premier League and was a mainstay in the Republic of Ireland set-up during his time with both clubs.
Following the conclusion of the 2002 World Cup and one season in the second tier with Coventry, Breen joined West Ham United on a free transfer.
Coventry signed exciting forward Peter Ndlovu to England from Highlanders in the players homeland of Zimbabwe. His Sky Blues career got off to a dream start with a debut goal at Highbury, followed by a thunderbolt winner against Aston Villa at Highfield Road.
In 1992 he became the first African player to feature in the Premier League and became a fans favourite with his performances in a Sky-Blue shirt.
The following season saw Ndlovu in his best form, and was subject of a £4 million bid from Arsenal, which saw Bobby Gould resign in response to the imminent sale of Coventry’s star man. Ndlovu stayed however and became the first away player to score a hat-trick at Anfield for over 30 years.
Peter moved on the Birmingham City in 1997 for £1.6 million, dropping down a division in the process. He helped Blues to two successive play-off appearances, but failed to reach the same heights he had in the Premier League for the Sky Blues. Ndlovu managed four seasons and over 100 appearances in Royal Blue before departing in 2001.
Born in Nigeria, Adebola moved to England as a child and began his football career in the prestigious Crewe Alexandra academy. He spent six years as a professional with the Railwaymen before First Division Birmingham City came calling in 1998, paying £1 million for the big striker’s services.
His Birmingham career began positively and Adebola scored 21 goals in his first 18 months as a Blue, however he fell out of favour in the months that followed and a move to Las Palmas fell through at the eleventh hour on medical grounds.
Despite being on the transfer list Adebola played his part, and he helped Birmingham to the 2001 League Cup Final where he started up front in a cruel penalty shoot-out loss to Liverpool.
Adebola wound up at Coventry via one season at Crystal Palace and joined the Sky Blues for the 2003/2004 season. He spent two short loans spells in the early part of his Coventry career at Burnley and Bradford, before establishing himself as a first team regular in 2005.
Adebola was part of an attacking force alongside Stern John and Gary McSheffery that saw the Sky Blues finish 8th in their first season at the Ricoh Arena. Adebola stayed at the club until 2008, amassing 163 league appearances and 31 goals before departing for Bristol City.