| Tournament | Round | Shirley Winkler | Jacky Booth |
| 05.02.2006 Kempsey Challenge (NSW) | 8 | 283 | 276 |
| 04.02.2007 Kempsey Challenge (NSW) | 11 | 297 | 327 |
| 01.02.2009 Kempsey (NSW) | 3 | 338 | 421 |
| 30.01.2010 Kempsey Cup & Challenge (NSW) | 7 | 330 | 296 |
| 06.02.2011 Kempsey 2011 (NSW) | 3 | 351 | 346 |
| 05.02.2012 Kempsey (NSW) | 2 | 269 | 333 |
| 03.02.2013 Kempsey (NSW) | 4 | 355 | 315 |
| 02.02.2014 Kempsey (NSW) | 1 | 350 | 320 |
| 02.02.2014 Kempsey (NSW) | 9 | 336 | 281 |
| 04.05.2014 Ocean Shores (NSW) | 2 | 264 | 412 |
| 03.02.2019 Kempsey Challenge (NSW) | 5 | 322 | 387 |
| Head-to-head after 11 games | 6 | 5 | |
| Average score | 317.72 | 337.63 | |
| Spread: | -219 | 219 | |