Hailing from a horse family background – his great-grandfather was a jockey and a trainer, his grandfather was a trainer, and his father was a jockey and a trainer – Kawada started to ride when he was a third grader in the elementary school and grabbed some titles in the show jumping competitions in his junior high school ages. He also spent his school’s summer holidays at “Shigaraki Bokujo” to ride and take care of horses, where trainer Mitsumasa Nakauchida’s father manages.
After spending the three-year course for jockeys in JRA Horseracing School, he gained his JRA jockey license in 2004 and debuted in March of the year. His first win on the JRA circuits was at Hanshin racecourse on 20 March and took his first ride in group race at Chukyo two months later. He won 16 races in 255 starts in the rookie year.
In 2006, when he was granted the JRA’s freelance jockey, he took his first group race success and then got a chance to contest in the Japanese Derby with Super Hornet (by Rodrigo de Triano). His success stories in the highest classes opened in the 2008 Satsuki Sho (Japanese 2000 Guineas) with Captain Thule (by Agnes Tachyon), followed by the 2010 Kikuka Sho (Japanese St. Leger) with Big Week (by Bago). In 2013, he ranked second with 120 wins but did capture his first JRA award. By winning the 2012 Japanese Oaks with Gentildonna (by Deep Impact), the 2014 Oka Sho (Japanese 1000 Guineas) with Harp Star (by Deep Impact) and the 2016 Japanese Derby with Makahiki (by Deep Impact), he became one of the eleven riders in JRA history to have won all five Japanese Classic races. He also associated with Maurice (by Screen Hero) and Lovely Day (by King Kamehameha) in G1 races and has won 1,817 at JRA (as of 21 November).