The Tampa Bay Rays selected Rickard in the ninth round of the 2012 MLB Draft.

Rickard attended Bishop Gorman High School in Las Vegas, where he played baseball with his brother John, and the University of Arizona.

[10] In 2013 with the Bowling Green Hot Rods he batted .270/.390/.409 with 79 runs (3rd in the Midwest League), 78 walks (3rd), 16 HBP (2nd), 8 sacrifice flies (3rd), and 30 stolen bases (8th).

He recorded his first major league hit in his first game off of Ervin Santana of the Minnesota Twins.

On May 20, Rickard hit his first career lead-off home run to start a game against the Angels.

[12] Rickard played 79 games (primarily in right field) for the Orioles in 2018, hitting .254/.300/.413 with 8 home runs and 23 RBI.

Rickard started the 2019 season with Orioles, playing 42 games (primarily in right field) of .203/.304/.347 ball with two home runs and six RBI in 118 at–bats before being sent down to the minors on May 24.

On June 21, 2019, Rickard was claimed off waivers by the San Francisco Giants and assigned to the Triple–A Sacramento River Cats.

[23] On January 5, 2020, the Giants re-signed Rickard to a minor league contract that included an invitation to spring training.