| Webb Simpson (8) | ||||||
| # | Date | Tournament | Picker | Finish | Money | Tally |
| 1 | 21-Mar | Valspar Championship | Motown | T54 | $19,404 | $19,404 |
| 2 | 8-Aug | Wyndham Championship | Babe | |||
| 3 | 8-Aug | Wyndham Championship | Cutlobbers | |||
| 4 | 8-Aug | Wyndham Championship | Irish Bully | |||
| 5 | 8-Aug | Wyndham Championship | Poof | |||
| 6 | 8-Aug | Wyndham Championship | WWMH | |||
| 7 | 21-Nov | RSM Classic | LDL | |||
| 8 | 21-Nov | RSM Classic | Tennis | |||