At the time, Boyd and Andre Jellema told media they saw Key when he arrived at the restaurant with some acquaintances. After initially being rebuffed by Key's security, the pair managed to introduce themselves, said they had voted for him asked to have a photo taken with him.
Boyd said they had told him they were unemployed and it was their only night out for the year.
"Then, being cheeky, I said 'would you pay for the meal?' And he goes 'absolutely'. So we thought, 'great, we've saved $80 bucks', and couldn't stop saying what a good guy he was."
However, Boyd said when they told the manager "John's got our tab" he did not believe them. After checking with Key's security the pair were marched out and charged with breach of bail before they were put in the cells for the night.
Now Boyd is seeking $10,000 compensation from police for his night in the cells - and wants the PM to be his key witness, according to Fairfax.
He claims Key's Diplomatic Protection Squad (DPS) over-reacted in an "abuse of power", Fairfax reported.
Key's office has steadfastly rejected Boyd's version of events saying the Prime Minister was never asked to pay for the meal, and had not offered to pick up the tab.
Boyd was also later charged with theft from the Green Parrot of $82 - the cost of their meals - and breach of bail. But the theft charge was later dropped and a judge found no breach of bail occurred.
An Independent Police Conduct Authority (IPCA) report in 2013 found Key's DPS staff did not use excessive force.
In June, Boyd filed a civil case against the Attorney General, Fairfax reported, claiming he did not get the chance to ask Key to back up his claim before being pulled aside by the DPS, and that he had sufficient money to pay the bill.
His lawyer Chris Nicholls has now written to Key's office requesting a formal statement about the Prime Minister's recollection of the nights events, according to Fairfax. It is understood Key's chief of staff Wayne Eagleson wrote back saying a potential settlement offer was likely from police so Key could not get involved.
"The PM is perfectly entitled to not respond, but at the end of the day he has been a witness to an event and I have asked him for information that would assist in the resolution of the dispute," Nicholls told Fairfax.
A spokesperson for Key said the Prime Minister "would deal with the matter at that time" if called as a witness.
Police denied the allegations made by Boyd and plan to defend any proceedings.