Depends totally on the shape of the object that is placed in the wind stream. Aerodynamics do not necessarily behave the same on forward flow as it does in reverse flow. Separation drag and stagnation drag in reverse flow will likely be different unless the object being tested is symmetrically shaped.
The headwind is just slower due to the tailwind, the airflow never goes backwards over the vehicle unless the tailwind speed is faster than the vehicle... unlikely.
Regards, Neil Tucson, AZ
That difference depends more on the influence of the air on the shape than anything else. If you have an efficient shape pointing into the wind, the negative effect of a headwind can be less than the positive effect of a tailwind that reduces separation drag.
Think of an equilateral triangle presented in two ways to the airflow. In the first we point one of the convergence points of the triangle directly into the the air stream. This would give you a low stagnation drag and a high separation drag. Now reverse the flow 180 degrees and we would have a high stagnation drag and dare I say a high separation drag as well.
If that triangle were travelling across the ground with a constant HP and rolling resistance, a headwind (Low stagnation/high separation drag) would reduce the speed. However, a tail wind of the same speed under the same condition would lower the stagnation drag which in turn would reduce the separation drag resulting in a larger differential of speed.
Look at some of the cars out there and the tail fins and spoilers designed to generate down force. The work by creating a vacuum under and behind the car. If you take one of these cars and reverse them at high speed, those devices work like sails (or kites) why? What happens there? (rhetorical, they catch air)
When a tail wind blows up behind those same cars they in fact do catch air or, more precisely stated, the tailwind reduces the separation drag that is generated allowing the shape to move more freely through the air. (<-Specifically ignoring the loss of traction on the effect of speed)
My thoughts without doing a study - A tailwind in most designs will yield a higher gain in ground speed than a headwind will reduce speed in a shape that is designed to go fast straight ahead.