I played for at least 3 clubs in South Yorkshire

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Whilst not entirely South Yorkshire Jon Stead, Billy Sharp and Paddy Kenny all played for three or more Yorkshire teams. Danny Cadamateri played for five Yorkshire clubs.
 

Jamal Campbell-Ryce (Rotherham, Barnsley, United)
Michael Smith (Barnsley, Rotherham, Wednesday)
 
Guesty said:
If we were to expand the definition of South Yorkshire to include those clubs covered by Radio Sheffield, Warnock played for Chesterfield, Rotherham and Barnsley in addition to managing us.
Click to expand...

Using the Radio Sheffield catchment:

Leon Clarke. United, Wednesday and Chesterfield.
 
Piggy Curran. Us, them, and Donny.
 
1973Blade said:
Looks like Gordon Owen the closest, but he didn't play for us!

Gordon Owen - Wikipedia

en.wikipedia.org en.wikipedia.org
Click to expand...

I don't think anyone has played for all 5 S Yorks clubs (and thus not for the 6 Radio Sheffield/Hallam clubs either).

Chris O'Grady has also done 5 out of 6. He's missing Doncaster.

Tony Cunningham, like Gordon Owen, played for all the South Yorks clubs except for us, but he did not play for Chesterfield.
 

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