You should wear it a bit below where the cups slide around, more than everywhere else, but chip the edges and stuff as well. Expose the wood or whatever underneath, maybe. The checkerboard pattern probably has to be modified a little to suit the same perspective as the cups. Just make the squares a bit rectangley, wider then they are deep.
You get a lot of useful references if you Google Image Search for 'peeling paint' or 'chipped paint', if that's what you want.