When he was 15 years old he fought two students from the Musashi Ryu Jujutsu, called Hitotsubashi, and Kanzashi. Takamatsu at this time was nicknamed Kotaro. It was common practice for the challengers to fight three members of the Ryu they had challenged. The first two must be of the highest rank, the third maybe the oldest, but not the best. If all three were beaten, then the Kancho (founder) or Soke would fight them. One of Toda's senior students Kamiya (aka Shindo-kun) who was 25 years old, whom Toda had given the Menkyo Kaiden to, was the first to f ight. He fought Hitotsubashi who also had the Menkyo kaiden in the Musashi Ryu. They bowed then fought. kamiya grabbed Hitotsubashi's sleeve and preformed "Hikikomi Moguri Gata Ganseki Otoshi". His techniques was perfect, however the Musashi Ryu teaches you to move with the technique, giving a false impression to your opponent, that they have won. Kamiya, was kicked in the solar plexus stunning him. kamiya was out cold, and Hitotsubashi, was proclaimed the winner.
Takamatsu, then called Kotaro (Young Tiger), was next to fight. He had at this point never been beaten, and it was said that even at his young age he was an intensely dangerous fighter.
First he fought Hitotsubashi, who kept his distance from Takamatsu, trying to get Takamatsu to come closer to attack. Then suddenly Hitotsubashi attacked with a right punch. Takamatsu dropped to the ground and applied oni Taoshi. Hitotsubashi hit the ground, and was restrained by Takamatsu causing him to faint. Next Takamatsu fought Kanzaki, who was 29 years old, and called Kishin (demon spirit), by the Musashi Ryu. He was also ranked Menkyo Kaiden (some say that he was able to give mastership licenses to people). Kanzaki attacked firstwith afeint.
Takamatsu fell for this, and as a result Kanzaki broke Takamatsu's left elbow. Takamatsu countered this with Gyaku Ganseki Otoshi. Kanzaki was not able to escape this throw, this technique beat Kanzaki, and as he was being taken down he was attacked again by Takamatsu with a rib breaking Hijidome elbow strike, but the broken elbow, caused him to pass out. However, as Kanzaki he some how managed to slap Takamatsu's ears, causing one of the them to rupture (This was later the cause for him to be excused from military service, and also left him deaf in one ear). The two fighters were revived by Toda, and together the men talked for many hours about fighting arts. Kanzaki commented that he had visited many Doio's to fight, but he had never met anyone like Takamatsu.