| Answer | Crossword Clue |
|---|---|
| DETROITTIGERS | Four-time World Series winner |
| TORRE | Four-time World Series-winning manager |
| TORRE | Four-time World Series winning manager |
| LALAW | Four-time Outstanding Drama Series Emmy winner |
| LALAW | Four-time Emmy winner for Outstanding Drama Series |
| MADMEN | Four-time Emmy winner for Outstanding Drama Series |
| CINCINNATIREDS | Five-time World Series winner |
| STLOUISCARDINALS | Nine-time World Series winner |
| MINNESOTATWINS | Two-time World Series winner |
| BROOKLYDDODGERS | One-time World Series winner |
| STU | Three-time World Series of Poker winner Ungar |
| STUUNGAR | Three-time winner of the World Series of Poker |
