Round of 1618–21 Jun
Orlando City won after extra time
Quarter-finals
- Orlando CityT1winner(5) 2New York CityT1(4) 2
Orlando City won 5–4 on penalties
Match details
- MatchOrlando City2–2 (5–4 pens)New York City11 Jul 2019 · Exploria Stadium (Orlando, Florida)
- Atlanta UnitedT1winner2
Match details
- MatchAtlanta United2–0Saint Louis11 Jul 2019 · Fifth Third Bank Stadium (Kennesaw, Georgia)
- Minnesota UnitedT1winner6
Match details
- MatchMinnesota United6–1New Mexico11 Jul 2019 · Allianz Field (Saint Paul, Minnesota)
- Los AngelesT10TimbersT1winner1
Match details
- MatchLos Angeles0–1Timbers11 Jul 2019 · Banc of California Stadium (Los Angeles, California)
Semi-finals
- Orlando CityT10Atlanta UnitedT1winner2
Match details
- MatchOrlando City0–2Atlanta United7 Aug 2019 · Exploria Stadium (Orlando, Florida)
- Minnesota UnitedT1winner2TimbersT11
Match details
- MatchMinnesota United2–1Timbers8 Aug 2019 · Allianz Field (Saint Paul, Minnesota)
Final
- Atlanta UnitedT1winner2
Match details
- MatchAtlanta United2–1Minnesota United28 Aug 2019 · Mercedes-Benz Stadium (Atlanta, Georgia)
Sources: Wikipedia (CC BY-SA 4.0), API-Football · Data sources