Henry Bolte was Victoria's longest serving Premier.
The longest serving manager in the English premier league is Sir Alex Ferguson. Next is Arsene Wenger. But the longest serving ENGLISH manager in the premier league is Steve Bruce, who ranks third overall. ref. http://en.wikipedia.org/wiki/List_of_English_Football_League_managers_by_date_of_appointment
NSW Premier Bob Carr
Ryan Giggs in the Premier League
Sir Thomas Playford.
alex ferguson arsene wenger david moyes
Sheppard of Ipswich
I don't know what you mean by oldest, if you mean age or the longest. Longest serving manager is Arsene Wenger, the oldest is the same.
The longest serving managers are Alex Ferguson, Arsene Wenger , David Moyes, Rafael Benitz and Sam Allardyce.