199 was declared along this route on 8 August 1928, from the ferry at Taren Point, along Taren Road, to the intersection with Kingsway at Caringbah (and continuing northwards via the Taren Point ferry along Rocky Point Road to the intersection with Princes Highway, and southwards along Kingsway to Cronulla); with the passing of the Main Roads (Amendment) Act of 1929 to provide for additional declarations of State Highways and Trunk Roads, this was amended to Main Road 199 on 8 April 1929.
In August 1928, route 199 was established along the path from Taren Point ferry to Caringbah via Taren Road and Kingsway, with a continuation northwards through Rocky Point Road to Princes Highway and southwards along Kingsway to Cronulla. This designation was later formalized as Main Road 199 in April 1929 after amendments to the Main Roads (Amendment) Act of 1929.