Kevin Pressman is a legendary goalkeeper at Sheffield Wednesday and did move to Leicester after a long career at Hillsborough. Matty Fryatt might not be that much recognized from his time at Sheffield Wednesday but he was at Hillsbrough on a loan playing 9 league games and scoring 4 goals which is not a bad tally.
Going back a bit players such as Jack Sinclair and Peter Rodrigues comes to mind, fine professionals in both camps and representing both clubs and as well playing together in both camps. Sinclair played for Leicester City from 1965 to 1968 and was at Sheffield Wednesday between 1969 and 1973. Rodrigues joined Sheffield Wednesday from Leicester City in 1970 and spent the next five seasons at Hillsbrough.
Richard Creswell was a fine forward at Sheffield Wednesday and made a move to Leicester City that didn’t turn out as well as we would have expected. Cresswell was just on the fringe and moved on Preston North End. Leicester City paid a fee of £750.000 for Cresswell but with only nine league games to his name, he will never be seen as a success.
Kevin Pressmann and Chris Kirkland are two goalkeepers who have been in both camps. Pressmann did join Leicester City in the latter years of his career after being the first choice at Hillsbrough for a long number of years. Kirkland had a short loan spell at Leicester City and later joined Sheffield Wednesday on a permanent contract and played 85 league games for The Owls.
Mark Bright made the most out of his time at Sheffield Wednesday and will be fondly remembered from his time there, at Leicester City he never really managed to convince anyone how his great talent and moved on to Crystal Palace and build that special partnership with Ian Wright.
Guy Branston moved around in football and before playing a single first team game at Leicester City he was on the move. He had a brief spell with The Owls playing 11 league games from 2004 to 2005.
Former Leicester City hero and also captain at times, Simon Grayson, also had a short loan spell at Sheffield Wednesday during his days with Blackburn Rovers.
Former Leicester City manager Nigel Pearson had great impact at Sheffield Wednesday as a player spending seven years at Hillsborough between his spells at Shrewsbury Town and Middlesbrough. Craig Shakespeare also had a brief spell at Hillsborough during his playing days.
Lawrie Madden had a brief and short loan spell at Leicester City, but a totally different experience with Sheffield Wednesday, spending his best years in football at Hillsborough. Lawrie Madden played 212 league games for The Owls over a period of eight years from 1983 to 1991.
Larry May was seen as a massive talent and England potential while at Leicester City, but his career stalled a bit going into the mid 80’s and made a move, first by joining Barnsley in 1983 and from there moving to Sheffield Wednesday.
Forward Mark Robins also spent a while in both camps, and had a relatively good period with Leicester City. His stay at Sheffield Wednesday was brief and playing 15 league games and scoring 3 goals in the years of 2003 and 2004.
A list of players in both camps,
- Goalkeepers
- Kevin Pressman
- Chris Kirkland
- Martin Hodge
- Defenders
- Peter Rodrigues
- Lawrie Madden
- Joe Mattock
- Larry May
- Julian Watts
- Simon Grayson
- Midfield
- Scott Oakes
- Forwards
- Mark Robins
- Jackie Sinclair
- Richard Creswell
- Matty Fryatt
- Mark Bright
TCF - FILBERT WAY 
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