I believe there were several different Gordon Bennett Cups, there was certainly a car race. This was a team event for nations. The U.K. won once ( S.F.Edge) and as host the next year held the event in the Isle of Man. This race (in the I o M) was followed in later years as the R.A.C. Tourist Trophy.
I do not believe the Australian General who won the race home from Singapore in 1942 was even closly related to the American tycoon.
Grahame-White was noted for flying at night in a race from London to Manchester. The railway company having white washed the mainline's sleepers to aid navigation!