The 31-year-old has been released by Stoke City, along with another former Black Cats, Rory Delap, and currently is on the hunt for a new club.
Boro boss Tony Mowbray could be preparing to make Whitehead an offer, with the prospect of reuniting him in midfield with former Sunderland youth academy prospect Grant Leadbitter.
A couple of other Championship clubs though – Derby County and Burnley – are also believed to be interested in a player who was a key member of Sunderland’s side from 2004-09.