On 14 May 1942 three KNILM aircraft flew under the Bridge once in each direction. The "Bridge" formation was led by Captain Frans Van Breemen in DC-2 PK-AFK followed by Capt Peter Deenik in DC-3 PK-ALW and Captain Dirk Rab (with John Gyzemyter as Flight Engineer) in DC-5 PK-ADC.
The pilots were as skilled as any you would find but they were reprimanded as it was feared that their feat would inspire less skilled pilots to attempt it, as indeed several did during the war.
DC-3 PK-ALW is now preserved at the Queensland Air Museum as VH-ANR. I used to enjoy reassuring John Gyzemyter that his record of having flown under the Sydney Harbour Bridge twice in a DC-5 would never be broken.
Rgds