Complex sentence: In 2009, the boat club entered four boats (2 men and 2 women) in the May Bumps and was awarded the Pegasus Cup for the second time (previously in 2007), awarded annually to the most successful boat club in Cambridge.
Split into simpler sentences: In 2009, the boat club entered four boats (2 men and 2 women) in the May Bumps. The boat club was awarded the Pegasus Cup for the 2nd time (also won it in 2007), awarded annually to the most successful boat club in Cambridge.