Born in Madras, Sasikiran won the Indian Chess Championship for the first time in 1999 and won it again in 2002, 2003 and 2013. In 1999 he also won the Asian Junior Chess Championship in Vũng Tàu, Vietnam. Sasikiran completed the requirements for the Grandmaster title at the 2000 Commonwealth Championship. In 2001, he won the prestigious Hastings International Chess tournament. In 2003, he won the 4th Asian Individual Championship as well as the Politiken Cup in Copenhagen. Sasikiran tied with Jan Timman for first place in the 2005 Sigeman & Co Chess Tournament, which took place in Malmö and Copenhagen.