Or he could forfeit the cup on purpose, concentrate on building a stronger team, and then he can win the cup normally :P
you could still do that with my strategie, and i believe that should be the target for the most teams here anyway.
But sometimes i advise new team to concentrate on cups at the beginning, because it have less impact if you get 3 or 4th placed, and maybe it has even advantages when you don't get the 5th placed team - so that strategy depens lot on the team and the league.