The same force is applied to two skateboards. one rolls across the room and the other moves a few feet and comes to a stop. where was there more work done? the skateboard that traveled the shorter distance shows more work because there was more resistance. the skateboard that traveled the longer distance shows more work because it was lighter. the skateboard that traveled further shows more work because the distance was greater. the skateboard that traveled the shorter distance shows more work because the force was greater.

The longer you spend reading and thinking about this question,
the more defective it appears.

-- In each case, the amount of work done is determined by the strength
of the force AND by  the distance the skateboard rolls while you're still
applying the force.   Without some more or different information, the total
distance the skateboard rolls may or may not tell how much work was done
to it.

-- We know that the forces are equal, but we don't know anything about
how far each one rolled while the force continued.  All we know is that
one force must have been removed.

-- If one skateboard moves a few feet and comes to a stop, then you
must have stopped pushing it at some time before it stopped, otherwise
it would have kept going. 

-- How far did that one roll while you were still pushing it ?

-- Did you also stop pushing the other skateboard at some point, or
did you stick with that one?

-- Did each skateboard both roll the same distance while you continued pushing it ?

I don't think we know enough about the experimental set-up and methods
to decide which skateboard had more work done to it.