Irish convicts formerly involved at the Battle of Vinegar Hill during the Irish Rebellion of 1798 began an uprising against British colonial authorities in New South Wales, Australia.

Between 1788 and 1868 the British penal system transported about 162,000 convicts from Great Britain and Ireland to various penal colonies in Australia.

The Battle of Vinegar Hill was a military engagement during the Irish Rebellion of 1798 on 21 June 1798 between a force of approximately 13,000 government troops under the command of Gerard Lake and 16,000 United Irishmen rebels led by Anthony Perry. The battle, a major rebel defeat, took place on 21 June 1798 on a large rebel camp on Vinegar Hill and in the streets of Enniscorthy, County Wexford and marked the last major attempt by the rebels to hold and control territory taken in Wexford.

The Irish Rebellion of 1798 was a popular insurrection against the British Crown in what was then the separate, but subordinate, Kingdom of Ireland. The main organising force was the Society of United Irishmen. First formed in Belfast by Presbyterians opposed to the landed Anglican establishment, the Society, despairing of reform, sought to secure a republic through a revolutionary union with the country's Catholic majority. The grievances of a rack-rented tenantry drove recruitment.

The Castle Hill convict rebellion was a convict rebellion in Castle Hill, Sydney, then part of the British colony of New South Wales. Led by veterans of the Irish Rebellion of 1798, the poorly armed insurgents confronted the colonial forces of Australia on 5 March 1804 at Rouse Hill. Their rout in the resulting skirmish was hailed by as loyalists as "Australia's Vinegar Hill" after the 1798 battle of Vinegar Hill, where Society of United Irishmen rebels were decisively defeated. The incident was the first major convict uprising in Australian history to be suppressed under martial law.