IT was his political comeback attempt and many thought he had a chance to win the seat long embedded in the Nationals' heartland of Cowper.
On Sunday in Coffs Harbour, where his election day campaign started, Mr Oakeshott reflected on the result while officially conceding defeat to the Nationals' newcomer Patrick Conaghan.
He was highly critical of the smear campaign that he believes cost him the win.
Conceding a defeat would "break his heart" for everyone who had helped out.
- Read more: Conaghan claims victory in Cowper
"Hopefully everyone can stay connected because there's been a lot of gratitude from me the way people have come together," Mr Oakeshott told his supporters at a community market on May 19.
"There are big and complex issues in our local area. We're one of the poorest places in Australia, with high youth unemployment, still waiting for a highway to be built. And then there's the big national issues - climate change, First People, Newstart.
"Yesterday voted in a different way. Yesterday people voted for their pockets, voted for fear and some probably voted for the smear over the last few weeks."
He said it seems some voters were enchanted by what the Nationals had to offer in the last few weeks of their campaign while on what he described as the "beer tour" of Cowper.
"Fear, smear and beers is probably what got us yesterday," he said, saying he hoped there was considerable reflection around Cowper, and the rest of the nation over coming weeks, as to why that determined the vote.
"We have nothing to fear - we can be anything."
Mr Oakeshott, while bunkering down with supporters on Saturday evening as the count progressed, slammed the National Party's negative advertising as "rubbish" which had "divided the community". He had hoped pre-polling would have given him the upper hand, but it failed to deliver.
He urged supporters to reach over their neighbour's fences, regardless of political differences after the election, and do what's right for the community.
It was his second shot at the seat. This time there was a swing against him with Mr Conaghan holding on at 57 per cent of the two party preferred over Mr Oakeshott's 43 per cent.
His challenge - a good, clean campaign - he says, wasn't enough to sway the loyalty of the electorate to the National Party.
With more than 1000 supporters and volunteers uniting to champion Mr Oakeshott's tilt for Cowper, many were considerably shocked by the result and disappointed the Nationals resorted to a last-minute personal attack, rather than talking to the people.
Volunteer Phoebe Crane said she was "honoured" to work on the campaign regardless of the result.
She said the volunteers had become like family.
"We have over 1000 volunteers," Ms Crane said.
"We all come from different walks of life, ethnicity, but have come together."
Volunteer Harry Creamer said he had "high hopes " for Mr Oakeshott.
"Given his track record when in Government for example the money for hospitals, the university and the Pacific Highway, then there is his commitment to real action on climate change and his concern for social issues such as youth unemployment," Mr Creamer said.
Mr Creamer said he was feeling "very despondent" and was bewildered at the result.
On Saturday night Mr Oakeshott, when asked by a supporter if he'd be back in four years' time, said he didn't know if he had it in him.
"It wasn't about me it was about getting something else going in this area that is about the values of the place we live in, the respect, inclusiveness, decency we all want from the area," Mr Oakeshott said.
"Good people have come together and put aside their own history and joined together in their white shirts and to try and make something special happen."