2. Gautam Gambhir (65 wins):
The discarded India opener began his IPL career with Delhi Daredevils in 2008 and was appointed the captain of the team in 2010 where he led the team to fifth place. In the following season, he was bought by Kolkata Knight Riders and was appointed the skipper of the team right away. In his first season, he led them to the playoffs. In the next season, he went one step better and led the side to their first title in 2012 by defeating defending champions Chennai Super Kings. In 2014, he led them to the title once again, defeating Kings XI Punjab in the final.
Overall, he has led in 112 IPL matches, won 65 and lost 46 of them at a win percentage of 58.48.