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