He was treated at the scene before being flown to St George Hospital in Sydney's south in a critical condition.
Despite hospital staff's best medical efforts, the man died last night.
Officers from Wollongong Police District are investigating the incident, and a report will be prepared for the Coroner.
A handful of people had already logged being swooped by the Nicholson Park bird on Magpie Alert, a website that tracks magpie attacks around Australia.
"Attacked twice cycling north, just helmet hits. On the cycling path, right behind Woonona Surf Club. They nest in the pine trees," a cyclist named Mike wrote in August.
A man walking through the park was swooped on September 13 as well as a cyclist.
On August 31, a cyclist named Jenny called the Nicholson Park magpie a "very determined bird".
"Magpie swooping from Norfolk pines by Surf Club. I cycled on the road to try and avoid it on my way back but the magpie chased me. A very determined bird," she wrote.
Two other cyclists reported being hit on the helmet by the bird.
Magpie swooping season is at its worst in early September when the birds begin to have babies and protect their young.
Earlier this month, a Sydney council killed a magpie after a cyclist complained about its aggressive swooping.
The cyclist, who said she was attacked a few weeks ago while riding near Old Windsor Rd in Bella Vista in northwest Sydney, complained to the Hills District Council.
Posting to a local cyclist Facebook group, the woman said she'd received a notice that the bird had been "removed", just weeks after she'd notified the council of the attack.
"I have just received an email advising that the magpie has now been removed, so hopefully that area will now be safe :)," the woman wrote on Facebook.
News.com.au understands the magpie was the source of a large number of bird attacks over the years and had caused significant issues for people travelling on the cycleway.
Before it was shot, a significant number of locals had complained about the bird.
