A gentleman by the name of Red Kelly realised that the water-ski section of the Club was increasing in numbers to the extent that a competition should be organised for the skiers. Although he was a sailor himself, he generously presented a cup for the winner.

Red had been in the Fleet Air Arm and had flown many aircraft including Swordfish, Seafire, Spitfire and Hurricanes, so it seemed natural to call the event the Fly Navy Cup. The first year it was an endurance event - the winner was the skier who could go the furthest without falling! The next year with standards improving, Dave Webb introduced a fancy dress element to the competition with 50% of the score being awarded for the costume. There is no longer fancy dress requirement, but the format remains the same.

The team consists of one boat, a driver and three skiers, each competing in a different discipline over a set course. The Junior Fly Navy Shield was introduced in 1988 and uses the same course as the senior event but has only one skier using the discipline of his or her own choosing.