In fact, I do not understand what you mean by saying
Pakistan managed to win the trophy only twice out of 14 attempts.
He means to say that Pakistan has played in 14 Asia cup till now and in those 14 occasions, they have managed to win the trophy only 2 times, meaning Pakistan are the Asian cup champions two times as compared to India who has won seven times and Srilanka who have won it six times.
Anyways, it's only for record purposes and people do not remember the history.