Matthew Wallace Kaskey (born March 17, 1997) is an American professional football offensive tackle who is a free agent.

In 2014, New Trier reached the Class 8A state playoffs with an 8–1 record; Kaskey led the team as a captain and was named to the All-Chicagoland, all-conference, and all-area first-teams at the conclusion of the season.

In addition to football, Kaskey also participated in track, lacrosse, and wrestling during his high school career.

Kaskey attended Dartmouth, where he played offensive tackle for the football program for four years, beginning in 2015.

In Kaskey's sophomore season, he started eight games and was named an All-Ivy honorable mention for his work at left tackle, where he would play for the rest of his collegiate career.

Kaskey signed with the Los Angeles Rams as an undrafted free agent following the 2019 NFL draft.