Generation War
In August 2019, Diamante began touring with Dragon Gate. He was announced as being the newest member of the heel stable R.E.D. He made his debut on August 7, during The Gate Of Adventure tour, alongside Kazma Sakamoto and Takashi Yoshida, defeating MaxiMuM (Dragon Kid, Jason Lee and Kaito Ishida). On December 15, at Final Gate, Diamante, Yoshida and H.Y.O defeated Strong Machine Gundan (Strong Machine J, Strong Machine F and Strong Machine G) and Natural Vibes (Kzy, Genki Horiguchi and Susumu Yokosuka) in a three way match to win the Open the Triangle Gate Championship. Shortly afterwards, Diamante was involved in a "Generation War" storyline, when following on from Último Dragón's ongoing feud with R.E.D, the wrestlers who were trained by Dragón joined him to fight against the stable. This led to wrestlers who were trained in the Dragon Gate dojo to band together and suspend the stables they were in as well, in order to establish the superior generation. On February 7, during the Truth Gate tour, Diamante, Yoshida and H.Y.O were defeated by Team Toryumon (Dragon Kid, Kenichiro Arai and Ryo Saito) in a three-way match, also involving Team Dragon Gate (Keisuke Okuda, Strong Machine J and Yosuke♥Santa Maria), ending their reign at 55 days. At King of Gate, he defeated Dragon Kid in the first round, Yosuke♥Santa Maria in the second round, before being defeated by Yamato in the quarter-finals.