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Cameron McGregor, 34, has been jailed for eight years for a 14-year campaign of violence and rape against five women, spanning from 2008 (when he was 16) to 2022 in Dundee and Newport-on-Tay, Fife.
At the High Court in Edinburgh, the trial revealed he punched and struck three women, while subjecting two others to repeated rapes.
The former scaffolding firm owner denied the charges but was convicted.
Defence solicitor advocate Kris Gilmartin noted McGregor served in the Army before a medical discharge and ran a business: "Prior to his remand he had 10 employees all of whom have now been made redundant."
McGregor was placed on the sex offenders register indefinitely, and Judge Lord Ericht issued non-harassment orders barring contact with his victims.
Det Insp Gordon Patullo said:
"McGregor is an abusive individual who subjected his victims to years of horrific offending, and he will now face the consequences of his actions."