Pokemon always made Ash win everything that has an important title to competitors. When he made to second spot, it's because they don't want him to be the top winner at everything all the time. I remember in an early season, he lost a battle in a league.
He will fail in some matches, but not an important match like, for example, the match that will decide who will get the master title. Every match is important to him, but they will make him fail a match from time to time.
We all know that the series will end some day with him winning the big thing XD