** = denotes CAP mainstage debut
| Role | Actor |
|---|---|
| Annie | Madeline Davis |
| The Orphans:
Molly |
Elayne Forristall |
| Miss Hannigan | Emma Adams ** |
| Bundles McCloskey (and Oliver Warbucks understudy) |
August Nau |
| Apple Seller | Warbucks Staff | Chloe Williams |
| Dogcatcher | Orphan | Lydia Davis |
| Sandy | Orphan | Aurora Grooters |
| Lt. Ward | Warbucks Staff | Hank Jones ** |
| Grace Farrell | Grace Narber |
| Drake | Griffin Sutten |
| Cecille | NY Citizen | Charly Proctor |
| Annette | NY Citizen | Abby Aldrich |
| Mrs. Greer | NY Citizen (and Annie understudy) |
Alison Keeler |
| Mrs. Pugh | NY Citizen | Madison Becthold |
| Oliver Warbucks | Cael Newman ** |
| Star-To-Be | Warbucks Staff | Megan Conrad |
| Woman in Brownstone Window | Orphan | Annabel Narber |
| Usherette | Orphan | Ella Jacobs ** |
| Radio Announcer | Orphan | Ella Oberhart |
| Rooster Hannigan | Aidan Farrell |
| Lily St. Regis | Morgan Lewis ** |
| Sound Effects Person | NY Citizen | Warbucks Staff | Megan Witzenburg ** |
| Bert Healy | NY Citizen | Warbucks Staff | Nick Meredith |
| President Franklin Delano Roosevelt | NY Citizen | Kyle Oliver |
| Louis Howe | NY Citizen | William Brown |
** = denotes CAP mainstage debut