We look at three players who have played for both City and Southend ahead of our clash with them at the Ricoh Arena...
Coventry City take on Southend United on Monday night and one of our current players will come up against his former side.
We'll also be coming up against one of our former players who could play in the heart of midfield against us at the Ricoh Arena...
Jacob Murphy
Murphy played for Southend United on loan back in 2014.
He played eight times for the Shrimpers in his second loan spell away from Norwich.
Frank Moussa
The Belgian made his name in England with Southend, who gave him his first professional debut all the way back in 2006.
Moussa was held in really high regard during his time with United, particularly with the fans as he was part of the side that earned promotion to the Championship.
Leicester City then came in for midfielder in 2010, before he became a cult hero with City during his spell between 2012-14.
GARY DEEGAN
We could be welcoming Gary Deegan back to the Ricoh Arena.
Arguably his finest moment in a City shirt came in a 2-2 against Leicester City, where he scored a crucial late equaliser.
The midfielder then moved to Scotland with Hibernian for the 2012-13 campaign, where he made 23 appearances, scoring once.
After a spell at Northampton, the tough tackling midfielder signed for the Shrimpers in 2014.