The Wai-Wai Shield and Malloy Shields are handicap events that have been competed for annually since the early 1900s. Today the Wai Wai Shield is swum on the Herne Bay to Curran Street Beach course. In earlier days it was swum among boats moored in Westhaven waters, and between the present cement wharf and the old salt water baths at the foot of Shelly Beach Road. Later it was swum on a triangular, there-and-back course around boats moored off Herne Bay Road and Sentinel Road Beaches. Wai-Wai shields have been presented to fastest male and fastest female since 1980.
The Malloy Shield was first presented in 1912 and was for many years swum from Chelsea Sugar Wharf to the old Shelly Beach baths. After these were demolished to make way for the Harbour Bridge, the finish line was shifted to Curran Street Beach. Reversing this swim to finish at Chelsea coincided with the formation of Auckland Central Masters Swimming (Inc) and the Chelsea Sugar Refining Co Ltd Centenary in 1984, when the late Bert Raper arranged sponsorship with Chelsea Sugar and the use of their magnificent facilities.
Also awarded at the Chelsa is the Osborne Cup for fastest female, and the Mazzoleni Cup for first male. These trophies were first presented in 1939 and 1979 respectively.
The Bays and Rangitoto Swims were sponsored by Eagle Technology Ltd from 1986 until 2013. The late Trevor Eagle was a member of the Ponsonby Swim Club and was instrumental in establishing the swims in the early 1980s with Bert and Mamie Raper. In 1986, the Bays Swim Cup sponsored by Eagle Technology was awarded for the first time at the inaugural Freyburg Wharf to Tamaki Yacht Club swim. Shortly afterwards, the Rangitoto-St Heliers event (previously administered under Eastern Suburbs Club as the Paul Kraus Cup) joined with the Auckland Central Masters and their sponsors to establish the Eagle Technology Rangitoto Cup.