He was appointed a full judge of the Supreme Court on 11 February 1907 following the resignation of Mr Justice W. G. Walker in February of that year. Street principally presided in bankruptcy, divorce and probate cases. He was also deputy president of the now abolished Court of Arbitration which dealt with industrial disputes between employer and employee, as well as setting minimum wage standards in the State. Street also sat in the now abolished Vice-Admiralty Court, first established in New South Wales during the time of Governor Arthur Phillip to deal with maritime disputes. In 1915, one of his sons, Lieutenant Lawrence Whistler Street, for whom Sir Laurence Whistler Street was named, was killed in action in Gallipoli serving the Allied forces in World War I. Lawrence volunteered for national service in August 1914, making him one of the earliest of his generation to do so. In 1918, Street was appointed the Chief Judge in Equity. The appointment of Street as Chief Justice marked a new beginning for the Australian legal system in the appointment of the senior judge of the court and a wholly Australian-trained lawyer as Chief Justice of Australia's first Supreme Court. Street was also appointed a Royal Commissioner on many occasions. The most significant of these were concerning the administration of the Returned Soldiers' Settlement Branch of the Department of Lands in 1921 and the case against the Industrial Workers of the World in 1918. In the latter commission, IWW was an organisation that promoted the concept of one big union. In Australia, they were active in campaigning against World War I. One campaign led to a police officer being shot and killed for which two members were found guilty and hanged. At the time of the Royal Commission, twelve members were still in jail for offences such as sedition. Street's commission concluded that some men were guilty and some were not. Most were subsequently released. Street's elder son, Kenneth Whistler Street, became a judge of the Supreme Court of New South Wales while he was himself. According to biographer Percival Serle, this is possibly the first time that a father and son sat have together on the same Supreme Court bench. Street was acting Chief Justice in 1924 as he was the senior judge of the court at that time. He became Chief Justice on 28 January 1925, succeeding Sir William Cullen. Sir Philip occupied that office until his seventieth birthday in 1933. According to the Supreme Court, he resigned his commission although Serle notes that he actually retired. Whatever is correct, he was the second longest serving judge in New South Wales. He was appointed Lieutenant-Governor in 1930, and administered the government in the absence of the Governor from May to October 1934, January to February 1935, and January to August 1936.
Members of the Street family have been prominent in law, politics, civil service, and the military, especially in Australia and in the state of New South Wales, since the 19th Century. The Street family is the only dynasty in Australian history with three consecutive vice-regal appointments to their name; men of the 2nd through 4th Australian generations of the family having become Chief Justice of the Supreme Court of New South Wales and Lieutenant-Governor of New South Wales. The patriarch of the Street family juridical tradition is Sir Thomas Street, who was made Chief Justice for Brecknock, Glamorgan and Radnor in 1677, and Baron of the Exchequer in April 1681. Sir Thomas had his children by Lady Penelope Berkeley, of the Berkeley family.
