Roldan was named the 2013 Gatorade National Player of the Year in soccer while attending El Rancho High School in Pico Rivera, California.

[3] He declined invitations from the LA Galaxy and Chivas USA to join their academy teams and led the El Rancho Dons to an undefeated season with 26 wins.

[6] In his two seasons of college soccer, Roldan made a total of 41 appearances and tallied 10 goals and seven assists as he helped lead the team to a Pac-12 title in 2013.

[12] On January 8, 2015, it was announced that Roldan had left college early to sign a Generation Adidas contract with Major League Soccer.

[16] Roldan developed into a deep-lying midfielder and earned a regular place in the starting lineup under head coach Sigi Schmid following his performances as an "impact substitute".

[21] He also played all eight matches in Seattle's run to the 2022 CONCACAF Champions League title, providing one goal and five assists, and was named to the Team of the Tournament.

[31] On July 12, 2017, he was cap-tied to the United States national team by starting their 2017 CONCACAF Gold Cup group stage match against Martinique.