The San Diego Padres selected Ross in the first round of the 2011 Major League Baseball draft (25th overall).

The San Diego Padres selected Ross in the first round of the 2011 Major League Baseball draft (25th overall) out of Bishop O'Dowd High School in Oakland, California.

[2] In 2012, he pitched for the Fort Wayne TinCaps of the Single–A Midwest League but ended up missing most of the season on the disabled list with right shoulder inflammation after being unable to make a May 10 start against the South Bend Silver Hawks due to tightness.

[12] On August 6, manager Matt Williams announced Ross would remain in the rotation and veteran starter Doug Fister would move to the bullpen, in recognition of the rookie's strong performance since his promotion.

He started the year pitching for the Class-AAA Syracuse Chiefs, but after Nationals starter Jeremy Guthrie was shelled for 10 earned runs in less than an inning in what would be his only appearance of the season,[19] Ross was called up.

[22] However, in the last of these starts, against the Atlanta Braves on July 9, Ross exited in the fourth inning as the velocity of his fastball dipped so low into the mid-80s that the stadium radar gun was registering them as changeups.

After recovering from his surgery, Ross attempted to make his first MLB start in 14 months on September 7, 2018, facing the Chicago Cubs on a rainy evening at Nationals Park.

[27] Ross started game 5 of the 2019 World Series for the Nationals in place of Max Scherzer, who was dealing with a back injury.

[28] On August 17, 2021, Ross was placed on the injured list after suffering a partial tear of his ulnar collateral ligament in his right elbow.

[30] On January 30, 2023, Ross signed a minor league contract with the San Francisco Giants organization.

[33] He began the season pitching out of Milwaukee's rotation, and compiled a 2–4 record and 4.50 ERA with 35 strikeouts across 9 starts.