Fill in any holes on your tabletop with wood putty. Run a putty knife over the repairs to remove excess putty. Allow the putty to dry. Lightly sand the repaired area so it is the same as the surrounding surface. Spot-prime repairs with a dab of primer and a foam brush.
Lightly sand a glossy surface with a sanding block. Wipe off the tabletop with a tack cloth.
Roll an even coat of paint over the entire top of the table. Use the lighter of the two colors for this base color. Let the paint dry overnight.
Measure the side of your table. Divide this number by 8 to determine how big to make each square on your checkerboard. Use a piece of chalk and a yardstick to mark out your grid.
Place strips of tape just inside the lighter squares. Use a razor to cut the ends of the tape straight across. To prevent confusion, place an X made of tape in each light square.
Roll out the dark squares with a foam roller. Roll in both directions to evenly disperse paint. Peel off the tape as soon as you finish painting each dark square.