Sam Hutchinson started his career at Chelsea before moving to the Owls.
The Owls head to Stamford Bridge for Sunday's FA Cup fourth round clash against the holders. Here, we look back at some of the players to have represented both teams.
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The Romanian arrived at Hillsborough in 1994 following an impressive World Cup for his country. He impressed in just over a year at S6 before earning a move to Chelsea, where he spent five seasons.
Barkley caught the eye in his short stint at Hillsborough in 2012. He hit four goals in 13 games before being recalled by Everton. Barkley, an England international, earned a 15million move to Chelsea in January 2018.
Hector arrived last summer at Hillsborough on a season-long loan from Chelsea. The Owls became his 16th different team, although he has yet to make an appearance for his parent club.
A firm fans' favourite at Wednesday, Hutchinson came through the ranks at Chelsea and made a handful of appearances before the Owls snapped him up in 2014. He has since played over 100 times for Wednesday.
Israel striker Sahar joined the Owls on loan in 2008, making 12 appearances and scoring three goals. He was loaned out twice more by parent club Chelsea, for whom he played just three times, before being sold to Espanyol in 2009.
Centre-half Thome arrived at S6 from Portugal and impressed sufficiently enough to earn a big money move to Stamford Bridge just two years later. He played in the famous Champions League win against Barcelona but was cup-tied for the last FA Cup final at the old Wembley - which the Blues won 2-0 against Aston Villa.
Striker Knight began his career at Chelsea but only ended up making one appearance for the Blues, in a UEFA Cup clash. He was farmed out on loan four times by the club, and during his temporary stint at Hillsborough (2002-03) he scored three goals.
Baker arrived at Hillsborough from Chelsea in 2014 and made his full league debut but failed to shine in Sheffield. Still on the Blues' books but has again been farmed out this season, to Reading.