 Considered one of the league's best umpires of his time, Ryan umpired in five Grand Finals between 2008 and 2011 (which included both the drawn Grand Final and replay in 2010) before temporarily retiring at the end of 2011 after 215 games.He returned to senior umpiring in 2015 after three years hiatus, and umpired his sixth Grand Final in 2017 at the age of 42, and his seventh in 2018.Ryan was generally criticised for his team's umpiring performance and subsequent defence of the criticism following the 2019 AFL ANZAC Day clash between Essendon and Collingwood.