The 23-year-old has agreed a deal for the remainder of the 2017/18 season after mutually ending his time with SkyBet Championship side Wigan Athletic.
Whitehead is no stranger to supporters at the Moss Rose, following two successful spells with the Silkmen.
A graduate of the youth set-up at Stockport County, Whitehead’s talent was quickly spotted and in the summer of 2013 he made the switch to West Ham United.
Unfortunately, he was unable to break in to the first-team with the Premier League Hammers and after a brief spell with Accrington Stanley, he joined Macclesfield in the summer of 2015 where he quickly became a fans` favourite.
After twenty-four appearances, then-League One Wigan swooped to sign the midfielder, with Whitehead remaining at the Moss Rose on loan for the rest of the 2015/16 campaign.
He returned to Wigan for the start of the 2016/17 season before making a loan move to League Two Cheltenham Town.
After a frustrating spell with the Robins, he would once again return to the Moss Rose in January 2017 on loan for the remainder of the 2016/17 season.
A hernia injury meant he was limited to just nine league appearances during that spell with John Askey’s side, but he did score a crucial goal to help Macclesfield past Forest Green Rovers in the Buildbase FA Trophy.
Now back at the Moss Rose once more, Whitehead will be keen to add to his fifty-one Silkmen appearances and re-capture the form of his previous spells with the club.