It always matters. A pro player is the lucky person who has the skill and mental motivation to get the job done. It is a very rare person that has both of these things. Some people have the drive but not the skill. Some have the skill but not the desire. At younger ages it is important to have positive experiences that will encourage a youngster to continue to love the game. That does not mean winning all the time but it does not mean losing all the time. There should be a good balance of both. That balance is different for each child. Too many wins too young can be a bad thing. Look at Al Parker as an example. He won the double grandslam for juniors at 12.
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