Takes place right after the events of The Million Dollar Tip (2014). Focuses on Will and how he is coping with the death of his best friend Evan, when all of the sudden his life is turned upside down once again by the mysterious Tip Man.
| Writing | Evan Pride | Writer |
| Directing | Evan Pride | Director |
| Writing | Will Hawkins | Writer |
| Directing | Tate Becherer | Director |
| Writing | Tate Becherer | Writer |
| Writing | Ryan Cardwell | Writer |