Complex sentence: He played against Canadian Vasek Pospisil in the second round and him defeated in three sets and with that win, he became the first man to win 300 matches at the masters 1000 level.
Split into simpler sentences: He played against Canadian Vasek Pospisil in the second round, defeating him in three sets. With that win, he became the first man to win 300 matches at the Masters 1000 level.