Stacking strategy in tennis

This guy was good at tennis

This is a placeholder for addressing a question from a friend of mine. You are the manager of a tennis team and your squad is going to play $n$ matches against another squad. Your players have a clear ordering 1 through $n$, as does the other team. Traditionally 1 plays 1, 2 plays 2, and so on.

If your goal is to maximize your expected number of wins, what is the ideal way to reorder your players assuming that the opposing coach will keep his in 1 through $n$ order?

What if your goal is to maximize the probability of some outcome? Like, what there are six matches and you want to maximize the probability that your team wins at least 3 of the matches? (A 3-3 tie is acceptable to you, but not acceptable to the other team.)

At first glance, the solution to the first problem seems to be to arrange your team $(2, 3, 4, \ldots, n, 1)$, but the answer to the second might be $(n, n-1, \ldots, 2, 1)$.