The club began preseason by spending two days in Lewis Center, Ohio before traveling to Chula Vista, California, for a week-long training camp.

On January 21, Columbus announced the addition of two friendly matches, both taking place while the club trains in California and behind closed doors.

[1] An ACL tear to Milton Valenzuela ended his 2019 season before it ever started, which caused Crew SC to acquire former player Waylon Francis for cover.

Robinho would come in to the game in the 79th minute to make his Crew SC debut, while Waylon Francis made his return to the Black and Gold after spending the 2018 season with the Seattle Sounders.

[9] Columbus visited Philadelphia on March 23 and suffered a heavy 3–0 defeat as Crew SC had two debuts for the club: Joe Bendik and JJ Williams.

A headed goal from Josh Williams from a Higuaín set-piece, as well as a double yellow card by the Revolution's Michael Mancienne gave Crew SC a 1–0 win.

The following week, the club were blanked in Montréal on the 13th, and then travelled home for two straight games, a 3–1 loss versus Portland on the 20th, with the loan Columbus goal being scored by Santos via a chip over goalkeeper Jeff Attinella.

Crew SC pulled one back in the 75th minute when a Robinho corner slipped through goalkeeper Bill Hamid's hands and into the net.

[13] in the following match, Crew SC got back to their winning ways, beating an LA Galaxy side at home 3–1, with Zardes, Higuain and Hector Jimenez scoring the goals.

[15] The following weekend was a shutout loss at Minnesota United, with the only goal of the match coming in the 70th minute from former Crew SC player Ethan Finlay.

Colorado regained the lead in the seventh minute of first-half stoppage time, as Jonathan Lewis's low shot deflected into the near post.

In the 54th minute, Columbus equalized again when Federico Higuaín's cross found Gyasi Zardes, who redirected the ball past Tim Howard.

[17] Injury news befell the team, as Designated Player Federico Higuaín tore his ACL during this game and would miss the remainder of the season.

[18] Beginning in June, the final match before the Gold Cup break, Columbus took on New York City FC at home and scored first, with the goal coming in the 28th minute via a penalty kick taken by Zardes.

Columbus would wind up losing, as Nico Lodeiro scored in the sixth minute of stoppage time to put his club ahead 2–1 and snatch an away victory for the Sounders.