Detectives have charged a man following an investigation into historical armed robberies, including one where a shot was fired, on the state's Central Coast nearly 20 years ago.
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Two men armed with a firearm entered a jewellery store on Karalta Road at Erina around 2.50pm on October 25, 2001.
Police allege the men threatened staff before stealing cash and jewellery and were last seen entering a blue Holden Commodore sedan, being driven by a third man.
As the vehicle was fleeing the scene, police say one of the men leant out of the vehicle and fired a shot at an off-duty police officer, who was pursuing them on foot.
In a separate incident, just after midnight on Saturday, September 27 2014, police say two men armed with a handgun and knife entered a licensed premise on the corner of East Market and Windsor streets, Richmond.
The men threatened a staff member before stealing cash and were last seen running on East Market Street before entering a Holden Commodore sedan on Francis Street, police allege.
No one was injured during the incidents.
Detectives from State Crime Command's Robbery and Serious Crime Squad commenced an investigation into the incidents, which are believed to be linked.
A 47-year-old man was arrested at Camperdown about 10am Thursday following the investigation. He was taken to Newtown Police Station and charged with two counts of robbery while armed with dangerous weapon and shoot at person with intent to inflict grievous bodily harm.
Police will allege in court that the man was armed with a firearm during both armed robberies and fired a shot at an off-duty probationary constable at Erina.
The Glebe man was refused bail to appear at Newtown Local Court on Friday.
Investigations are continuing, and police are appealing for anyone with information that may assist detectives to identify other people involved.
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