This is one of the more even rivalries at the top of the sport. Felipe Pena and Gordon Ryan have met 4 times on record, and the split is 2-2 with no draws. Both wins for each man came in different phases: Pena took the first two meetings, at the 2016 Studio 540 Superfight by submission and the final of the 2017 ADCC World Championship on points, then Ryan answered with a submission at 2022 WNO: Gordon Ryan vs Felipe Pena and a points decision at the 2024 ADCC World Championship. Notably, all 4 meetings were no-gi.

Their broader records point to different profiles. Pena carries 152 wins against 27 losses and 3 draws over 182 recorded matches, an 84% win rate, with 46% of his wins coming by submission. Ryan sits at 94 wins, 4 losses, and 3 draws across 101 recorded matches, a 93% win rate, and finishes at a much higher clip with 78% of his wins by submission. Pena's most frequent finish is the Gi Choke From Back with 22 wins, while Ryan's is the Rear Naked Choke with 17.

What decided these four is worth sitting with. Two went to points and two ended in submission, and the outcomes flipped over time. The early pair went Pena's way, the later pair went Ryan's, which reads less like a clear stylistic edge and more like a rivalry that shifted as both men aged and evolved.