We take a look back at some of those to have represented both the Sky Blues and Southend United, ahead of this weekend's clash.
Jonson Clarke-Harris
Jonson joined Coventry as a youth player, working his way to make his first professional debut in 2010 and also setting the record for being the youngest player to play for the Coventry at 16 years and 21 days.
The striker departed in 2012 and moved to Peterborough, where he was sent out on loan to Southend United for month. Clarke-Harris played 3 games for Southend, before returning back to Peterborough at the end of the loan.
After leaving the Sky Blues five years before Jonson was reunited with club when being sent on loan from Rotherham in January 2018. After a successful loan spell, playing a part in the campaign that got Coventry back into League One, Jonson signed for the Sky Blues on a two-year deal at the start of the 2018/19 season.
Freddy Eastwood
Eastwood started his youth career at Southend United in 1997, developing in their system for two years before moving to West Ham academy in 1999. After being released from West Ham in 2003, Eastwood had a year out of football before returning at Gray’s Athletic. After a good season with the non-league side, he returned to the club he started at in Southend United scoring 49 goals in 111 appearances on his first spell back.
In 2007 Eastwood left Southend for fellow midlands club Wolverhampton Wanderers, where he played out the 2007/08 season. He then ended up joining the Sky Blues in 2009 and Eastwood became the first player to score a hat-trick at The Ricoh Arena.
After five seasons and 113 appearances with the Sky Blues, Eastwood’s contract expired seeing him make his final move back to Southend, where he would go on to make another 64 appearances for The Shrimpers before retiring from professional football in 2014.
Franck Moussa
The Belgium born midfielder moved over to England in 2002 as a youth player when joining West Ham. Still in his youth career Moussa moved to Southend in 2005. Leading on to making his first professional debut in 2006. After Southend made it to the championship in 2008, Moussa went on loan to Wycombe for 2 months, before returning into the Southend side until 2010.
After leaving Southend, Moussa joined Leicester and had loan spells at Doncaster and Chesterfield, before joining Coventry in 2012. In Moussa’s first season with the club, he went on to win the football leagues goal of the season. After two years, 77 appearances and 18 goals for the Sky Blues, Moussa left for Charlton.