Stephen Fleming:
Stephen Fleming is the disgraceful skipper of New Zealand. He led Kiwis in three World Cups in 1999, 2003 and 2007 but could not get his hand on trophies. However, his tactics and strategies can not be doubted after seeing his successful stint for the Chennai Super Kings as the coach. Also, he is the only captain on this list who has not won a world cup. He had hard luck and was unfortunate to lift the trophy.
In total, he has captained the team in 27 World Cup matches and won 16 matches whereas he has lost ten matches and one ended in a draw.