Brendan King finished work at a Liverpool factory at 12.59pm on April 29.
His colleague, Robert Adams, clocked on exactly half an hour later.
Those 30 minutes appear to have cost Mr King, a father-of-five, nearly $2.7 million, a share in a $40 million lottery jackpot.
It was on that afternoon that Mr Adams, who ran lottery syndicates at the cable manufacturing plant, decided to pool funds to enter the May 5 Powerball draw.
Mr King held a ticket in the same draw as part of an earlier syndicate, but Mr Adams formed a second, one-off syndicate of 14 people to boost their chances of becoming millionaires.
Even though Mr King was a regular contributor to the lottery pools at the Prysmian plant, Mr Adams simply did not think of including him in the second group because the pair did not cross paths on the factory floor.
The second syndicate won the $40,445,165.25 jackpot.
Mr King sued Mr Adams in the NSW Supreme Court, arguing he was entitled to almost $2.7 million because he understood he had paid to be included in all of the syndicates organised by Mr Adams.
But Justice John Sackar on Wednesday ruled that there were clearly two separate syndicates, with no mingled funds, and Mr King was not part of the winning group.
"I am satisfied that Mr Adams simply did not turn his mind to Mr King when he decided to form the winning syndicate and purchase a ticket on its behalf," Justice Sackar said.
"I accept Mr Adams' explanation that he did not cross paths with Mr King at work during the relevant period.
"No assertion was made to suggest Mr Adams' omission of Mr King was the result of any motive to do so.
"The winning syndicate was an afterthought."
Mr Adams described his method of organising the syndicates as a "dog's breakfast", involving wads of cash held together by bulldog clips, and payment records kept in exercise books and on pieces of cardboard.
Justice Sackar said that, while it was not a sophisticated system, Mr Adams' records corroborated evidence about the way he ran the syndicates.
"There is simply no evidence to suggest that Mr King was, or ever was intended to be, a member of the winning syndicate."
In his statement of claim, Mr King recalled hearing about the syndicate's win and telling a colleague, "I'm a part of that!"
But when he looked through a bundle of tickets in his desk drawer, he did not see the winning numbers.
He told Mr Adams: "Hey Bob, the lotto numbers have gone off", and Mr Adams responded "You're not a part of that."
Later in the week, the pair again spoke and Mr Adams allegedly told him: "Shit happens. I run a lot of Lottos."
Members of the winning syndicate emerged from court with smiles on their faces, but did not want to make a statement.
Mr King was not in court to hear the decision.
