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 | Will Hawkins | Writer |
| Writing | Evan Pride | Writer |
| Writing | Ryan Cardwell | Writer |
| Directing | Tate Becherer | Director |
| Writing | Tate Becherer | Writer |
| Directing | Evan Pride | Director |