Mr O'Connor will take over from John Morris in October as the 11th headmaster at the Auckland school. Mr Morris had held the position since 1993.
Mr O'Connor said yesterday that he and his wife relish memories of their time in Wairarapa and the friends the couple made in education circles and in regional hockey, a sport in which Mr O'Connor was a player, coach and international referee.
"We were reflecting last night about things from Masterton onwards. We really enjoyed our time there and I loved Wairarapa College. It's a fantastic school with some great people and it was a struggle for both Anne and I to leave."
Former Wairarapa College teacher Donald Simpson had quickly recognised Mr O'Connor as a superlative leader of the school's English department, he said, and "a man who was going places".
In 2007, Mr O'Connor was awarded a Sir Peter Blake Trust Emerging Leader Award and a Woolf Fisher Fellowship.
Mr O'Connor considers his upcoming appointment as "a new challenge", he said, which allays his fears of becoming "too comfortable and complacent" in his present position.
Auckland Grammar board of trustees chairman Jeff Blackburn said Mr O'Connor was an "impressive and extremely well-regarded principal in the New Zealand secondary school sector".