[1] As a freshman, she started in all 25 matches and tied for the most points (15) on the team playing as a forward (though initially recruited as a defender).

[4] As a sophomore starting in all 25 games, McCaskill led the team in points and goals (29 and 10 respectively) while her nine assists ranked second.

[6] After the team folded due to failed buyout negotiations in late January, McCaskill was selected by Sky Blue FC with the second pick in the 2018 NWSL Dispersal Draft.

[9] McCaskill was a finalist for 2018 NWSL Rookie of the Year, alongside Andi Sullivan and Imani Dorsey.

Before the 2021 Season Chicago traded McCaskill as well as Yuki Nagasato's rights to Racing Louisville FC as well as a 2021 International Roster spot and the No.

[16] McCaskill was Angel City's joint top scorer with Alyssa Thompson with four goals in the 2023 regular season.

On December 20, 2023, San Diego Wave FC announced the signing of McCaskill to a three-year contract.

[21] She made her debut with the Wave on March 15, 2024 in an NWSL Challenge Cup game against NJ/NY Gotham FC.

McCaskill assisted Alex Morgan on the game-winning goal, serving up a corner kick in the 88th minute of the match.

[22][23] On the last game of the Wave's 2024 season, McCaskill scored her first goal with the club in a 3–1 win against Racing Louisville FC.

[24] McCaskill has represented the United States on the under-23 national team and was nominated for U.S. Soccer's 2017 Young Female Athlete of the Year award.