Nestor Gorosito, head coach of Argentine powerhouse River Plate. I'm afraid even Keegan himself in his prime and current Newcastle defender Fabricio Coloccini cannot match Nestor's perm/mullet.
Mircea Lucescu, UEFA Cup winning coach of Ukranian side Shakhtar Dontesk. He co-wins for what seems to be his sheer lack of concern for how his hair looks. Judging by this picture, if he told me he had never once combed his hair in his life, I would believe him. Similarly, if he told me he combed it five times a day with an egg beater, I would believe him. There's no real way to define what's going on here. The top is permed and the sides are straight? I'm lost. Anyway, congrats to him on his victory.
Pim Verbeek, head coach of the Australian National Team. He wins for having Stage 2 terminal Costanza Balding Pattern but still living his life to the fullest anyway, damn it!