For  the Herne Bay and Chelsea Swims there are  several trophies awarded through the Ponsonby Amateur Swimming and Life Saving Club . These awards are restricted to registered members of recognised Swimming Clubs.

Wetsuits and late entries are not eligible for the following trophies.

The Wai-Wai and Malloy Shields are handicap events which have been competed for annually since the early 1900s. Today the Wai-Wai Shield is swum over the Herne Bay to Curran Street Beach course. In earlier days it was swum amongst boats moored in Westhaven waters, and between the present cement wharf and 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 Cups 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. The fastest female receives the Osborne Cup first presented in 1939 while the Mazzoleni Cup for the first male was not presented until 1979.