Kai Kobayashi has been taking part in walking competitions since 2013, initially on a national level. In 2014 he competed over 10 km at the Japanese University Championships, which he contested in a personal best of 39: 27.90 minutes. Over the 20 km distance it improved to 1:21:13 h. A year later, he managed to stay below the 1:20 h mark, for example at the Asian Walking Championships, where he needed 1:19:12 h for the 20 km, which is still his personal best over this distance and earned him fourth place. He confirmed the place a year later at the same championships. In 2016 he also took part in the team competition at the World Walking Championships in Rome, which the Japanese team could not finish.
In 2017 he achieved his greatest sporting success to date with the bronze medal from the World Championships in London. There he competed over the 50 km distance and secured third place with a personal best of 3:41:19 h. In 2018, the Japanese team was once again unable to finish the competition at the World Walking Championships in Taicang, China.