I've based this off players I thought were going to be good signings but turned out massive disappointments
Joe Hart
Danny Fox
Gentile
Gibson
Bikey
Mark Ford
Remco Van Der Schaff
Fernando Guerrero
Berisha
Weghorst
Liam Robinson
Burnley’s Biggest Flops XI
Re: Burnley’s Biggest Flops XI
Tommy Walker - signed from Stoke in about 1972 - came with a burgeoning reputation & disappeared without trace after a few Reserve games. Similar scenario with Willie Watson, a full back signed from Man Utd in 1973 - his Burnley 'career' doesn't even warrant a mention on Wikipedia.
Re: Burnley’s Biggest Flops XI
Hennings, Walters, Sordell, Jutkiewicz
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Re: Burnley’s Biggest Flops XI
Johnathon Walters? Didn't we get him on a free after Stoke got related? I didn't expect much of him apart from a backup sub forward, and that's pretty much what we got. File under worked as expected

Come to think of it after a few other have mentioned it, Eddie Howe would be up there. Big reputation as an up and coming young manager, fancied the challenge of getting Burnley back to PL, great work with Bournemouth before. Then absolutely nothing came of him in the 12 months he was here (apart from a few good signing he left us).
Looking at his managerial CV's, Burnley was his biggest flop.