May 8 2021: Olivia Woodruff places 2nd at the Women SW 4 Race at the Steamboat Roubaix - Hell of the High Rockies in a group sprint

Mar 28 2021: Olivia Woodruff places 10th at the Women Cat3/4/5 Race at the Maverick Classics - RR in a group sprint

Mar 27 2021: Olivia Woodruff places 7th at the Women Cat 3/4/5 Race at the Maverick Classics - Crit in a breakaway