1. Imagine a line of kids holding hands with a pole in the center. They are directed to proceed in a line around the pole. Those close to the center will have to move slower, those at the edge have a big circle to make..so they have to move faster (like the plane) All this makes one assumption that is not really valid..that the sun is directly overhead, and the shadow is directly below.
2. When the sun is at an angle an object may have a shadow that is longer than itself. If an object moves toward the sun, the shadow might not really move much, if it moves in another direction the shadow will cover more distance on the ground than is actually moved because it is streched out kind of.
Go out in the sun on an afternoon, place a pencil point on the ground then pick it up one inch, then measure the distance from the shadow's original location to it's new location...it will be more than one inch, and the distance will vary depending on if you move it an inch towards the sun, or away. If you moved it one inch per second...it's shadow would move more than one inch in the same second...faster.
The angle of the sun will very seldom be close to 90 degrees...only in the tropics and only at noon, even then only along a specific line of latitude. If you live in a temperate climate you never ever will see a 90 degree angle.
3. The earth is turning too...towards the East...15 degrees /hour (111km/hr at the equator). If you travel east your speed is reduced, if you travel west it is increased adding your speed to the earth's speed.
All in all...the shadows are going to be the biggest factor. The shadow could move faster or slower than the actual plane.