I had a foster kid for almost two years. We knew him before that because he was a customer of ours at the store my wife and I owned.
To the point, it was a game store. We never let Will win, but we did play with handicaps. One of the educational games that he actually didn't mind was the old National Geographic game where you lay down map hexes. He played on the low difficulty, my wife played on the medium difficulty, and I played on the highest difficulty. Scores came in fairly evenly.
In other games, it was a level playing field.