On January 27, 2015, the Rangers traded Ross to the Boston Red Sox in exchange for pitcher Anthony Ranaudo.

In 2015, Ross had a solid season posting a 3.86 ERA in 54 appearances, and even serving as the Red Sox closer for a brief time.

In 2016, Ross was an integral part of the Boston bullpen, appearing in 54 games, racking up 55+1⁄3 innings, to the tune of a 3–2 record and 56 strikeouts.

On June 19, 2019, Ross signed with the Sugar Land Skeeters of the independent Atlantic League of Professional Baseball.

On July 1, 2023, Ross signed with the Spire City Ghost Hounds of the Atlantic League of Professional Baseball.

[11] After allowing 2 runs (1 earned) on 2 hits and 2 walks across 1+1⁄3 innings pitched during his only appearance, Ross was released by the team the following day.

[11] On October 23, 2023, Ross was selected in the second round by the Mumbai Cobras, with the 12th overall pick, of the 2023 Baseball United inaugural draft.

[12] Ross pitched 1+1⁄3 innings for United All-Stars West in the league's inaugural showcase series, surrendering 2 runs (1 earned) on 3 hits and 2 walks.