In 2021, won his first Grey Cup with the Winnipeg Blue Bombers, going 5-for-5 on field goals attempts in the Grey Cup.
CFL and West Division All-Star in 2019.
B.C. Lions Most Outstanding Special Teams Player in 2019.
Hamilton Tiger-Cats Most Outstanding Special Team Player in 2017.
2021: (Winnipeg) In three regular season games, converted 7-of-9 field goal attempts and converted 5-of-5 field goal attempts in the 108th Grey Cup.
2020: (Houston Roughnecks/New York Jets) Selected by the Houston Roughnecks in the 2020 XFL Supplemental Draft, appearing in five games, before the league ceased operations in April. Castillo was then signed by the New York Jets on October 14, 2020 and made his debut in a Week 7 game against the Buffalo Bills. He was later released by the Jets in January of 2021.
2019: (B.C.) Appeared in 18 regular season games, converting 41-of-45 field goal attempts. West Division All- Star and CFL All- Star.
2017: (Hamilton) Played in 14 games, connecting on 29-of-34 field goal attempts and punting 93 times for a 45.1-yard average. Suffered a season-ending ACL injury in October, did not play in 2018.
2016: (Ottawa) Joined the RedBlacks in September for two games.
2015: (Winnipeg) Appeared in four games for the Blue Bombers, going 10-of-13 on field goal attempts and punted eight times for 43.5-yard average.