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Never. Even a kindergartner is sophisticated enough to know when she shouldn't have won and did. Altering the rules to let your child win teaches her that it is better to win than to play fair, which is exactly the opposite of what you want to teach her. Allowing her to lose will help her learn how to do it graciously.
Instead of bending the rules to let her win, find games that she can win fair and square. Games of chance like Go Fish and Candyland have remained popular, in part, because children are just as likely to win as their parents are.
You can also play cooperative games in which you work together instead of competing. Combining your skills to see how long you can keep a balloon in the air, for example, not only teaches your child the value of teamwork but also helps her to feel that she can accomplish things without "winning."
See our poll: How often do you let your child win?