Matthew Lamb, from Hull, says he believes the photo was taken between late 1928 and early 1929.
The cup, which was created in 1931, is awarded to Hull-born children for an act of bravery.
The 95th anniversary of aviation pioneer Amy Johnson's 10,000-mile flight to Australia will be marked.
Writer Jenny Lockyer says she will explore how the pioneering pilot "had a dream and made it happen".
The cup is awarded to Hull-born children who have shown "exceptional bravery".
The Hull-born pilot made history when she became the first woman to fly solo to Australia.
The pioneering aviator died when her plane crashed into the Thames near Herne Bay in January 1941.
The award for local children is inspired by the famous Hull aviator.
The piece is said to have been fished out of the Thames estuary by a Royal Navy sailor.
