1. Better Cardiovascular Fitness: Soccer Player or Cross-Country Skier?
2. Better Problem Solving: Engineer or Medical Doctor?
3. Better Spatial Orientation/Navigation Sense: Taxi Driver or Park Ranger?
4. Aerial Battle: Falconry vs Kite Flying?
5. Aerial Battle: Falconry vs Drones?
6. Visual Art Popularity Contest: Human vs A.I.?
7. Short Story Writing Contest: Human vs A.I.?
8. Handicapped Chess Match: see below
One side has 4 pawns, 1 bishop, 1 knight, and 1 rook, the other side has a queen, both rooks and no pawns.
9. Bike Race: Gravel Bike vs Mountain Bike
To make the race fair it would have to be a very long distance with a mixture of terrains that favour each type of bike in turn.