1. Kevin Blackwood vs. Christian Casanova
2. Ace Romero vs. DL Hurst
3. The Workhorsemen (Anthony Henry & JD Drake) vs. The Maine State Posse (DangerKid & Aiden Aggro)
4. Eli Everfly vs. JT Dunn
5. Anthony Greene vs. Tommy Dreamer vs. Shawn Spears
6. Daniel Garcia vs. Pepper Parks
7. Ashley Vox vs. Swoggle vs. Covey Christ vs. Lil Blay vs. Channing Thomas vs. Jeremy Leary
8. Skylar vs. Kris Statlander
9. Mark Sterling vs. Puf
10. 2019 Vacationland Cup Finals: Ace Romero vs. Anthony Greene vs. JT Dunn vs. Kevin Blackwood