Woollarawarre Bennelong (c. 1764 – 3 January 1813) was a senior man of the Eora, an Aboriginal Australian people of the Port Jackson area, at the time of the first British settlement in Australia. Bennelong served as an interlocutor between the Eora and the British, both in the colony of New South Wales and in Great Britain. He was the first Aboriginal Australian to visit Europe and return.

In 1789, he was abducted on the authority of Governor Arthur Phillip, who hoped to use Bennelong to establish official dialogue with the Eora people. However, Bennelong escaped after several months. A tenuous relationship subsequently developed between Bennelong and the colonists, with various attacks and reconciliations occurring throughout their ensuing association with each other. Despite this friction, he came to be a significant ambassador of the Eora.

Bennelong was taken to Great Britain in 1792 and he resided in London for three years. Eventually his health deteriorated and in February 1795 he was returned to Australia. Back in his homeland, Bennelong was rejected from British colonial society and branded an alcoholic "savage" for vigorously maintaining his connection to a traditional lifestyle. He became a respected leader of the surviving remnants of the various local Indigenous clans in the Sydney region. He died at Kissing Point in 1813, aged about 48, and was buried in James Squire's orchard.

Woollarawarre Bennelong, the son of Goorah-Goorah and Gagolh, was born circa 1764 on the south shore of the Parramatta River. He was a member of the Wangal clan, connected with the south side of the Parramatta River, having close ties with the Wallumedegal clan, on the west side of the river, and the Burramattagal clan near today's Parramatta. He had several sisters, Wariwéar, Karangarang, Wûrrgan and Munânguri, who married important men from nearby clans, thereby creating political links for their brother. The island of Memel in Port Jackson was part of his personal property, inherited through his father.

He had five names, given at different times during the various ritual inductions he underwent. The other four are given as Wolarrebarre, Wogultrowe, Boinba, and Bundabunda. According to British officer Watkin Tench, Bennelong preferred to be called Woollarawarre.

Bennelong was brought to the settlement at Sydney Cove in November 1789 by order of the governor, Arthur Phillip, who was under instructions from King George III to establish relationships with the indigenous populations. At that time, the Eora conscientiously avoided contact with the newcomers, and in desperation Phillip resorted to kidnapping. A man named Arabanoo was captured, but like many other Aboriginal people near the settlement, he died in a smallpox epidemic a few months later in May 1789. Bennelong was captured with Colebee on 25 November 1789 as part of Phillip's plan to learn the language and customs of the local people. William Bradley painted a watercolour of the occasion and described the capture in his journal as the "most unpleasant service" he was ever ordered to undertake. At the time of his capture, Bennelong's age was estimated at 25, and he was described as being "of good stature, stoutly made", with a "bold, intrepid countenance". His appetite was such that "the ration of a week was insufficient to have kept him for a day", and "love and war seemed his favourite pursuits".

Colebee soon escaped, but Bennelong stayed in the settlement for several months, then slipped away. Four months later, he was sighted by officers in Manly Cove, and Phillip was notified. The governor hurried over and approached Bennelong, who was with a group of roughly 20 warriors. Phillip took a gesture by Bennelong towards another Aboriginal man, Willemering, as an invitation for an introduction, and extended his hand to the latter, who responded by spearing Phillip in the shoulder. A scuffle broke out, but the officers managed to assist the governor away to safety where the spear was removed and a full recovery followed.

Willemering was a kurdaitcha of the Kayimai clan from the area now known as Balgowlah. It has been suggested by some historians that he had been enlisted by Bennelong to carry out payback for the latter's sense of personal injury on having been kidnapped. In this view, some form of atonement was necessary as a prelude to any further arrangements with the colonists. Phillip ordered that no retaliation take place and Bennelong, some days later, turned up to visit him as he was recovering from the wound, and their relationship was renewed. In a gesture of kinship, Bennelong bestowed upon Phillip the Aboriginal name Wolawaree and learned to speak English. In 1790, Phillip built a hut for him on what became known as Bennelong Point (now occupied by the Sydney Opera House).