Win, lose or draw
I know the schools of thought on this: Let them win and it gives them a taste of success and the incentive to keep playing. OR ... Let them win and you undermine their self determination and bolster their sense of entitlement.
I suppose I let Ittybit win a lot when she was little. I'd keep the game close, or as close as possible, until the finish. I didn't really think of it as "letting her win" so much as I assumed it was just putting handicaps on my advantage.
What I've shied away from are the celebrations of victory and the disappointed wailings of defeat. I always hated those particular points of competition. Win or lose, we'd just play another game.
So? Do you let them win?