Click on the years below to see past results. Please note the 2012 Fall challenges were cancelled due to Super Storm Sandy and the 2020 Fall challenges were cancelled due to COVID 19.
| Fall: | 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 | 2013 | 2012 | 2011 | 2010 | 2009 | 2008 | 2007 | 2006 | 2005 | 2004 |
| Winter: | 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 | 2013 | 2012 | 2011 | 2010 | 2009 | 2008 | 2007 | 2006 | 2005 |
2016 Fall Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Blair / Warner | 1 | 7 | Donovan / Leddy | Blair / Warner | 4-6, 6-3, 6-4 |
| 2 | 2 | Fox / Kloud | 1 | 6 | Augustine / Johnson | Fox / Kloud | 6-1, 6-4 |
| 3 | 1 | Brown / Howe | 2 | 7 | Baldwin / Laughton | Brown / Howe | 6-3, 6-0 |
| 3 | 2 | Ahrens / Grillo | 2 | 6 | Sibbett / Wheeler | ||
| 4 | 1 | Cooney / Owsley | 3 | 7 | Root / Tierney | Cooney / Owsley | walkover |
| 4 | 2 | Corcoran / Dunn | 3 | 6 | Beecher / Hladick | Corcoran / Dunn | 6-4, 6-3 |
| 5 | 1 | Dial / Radecki | 4 | 7 | Gelnaw / Karr | Dial / Radecki | walkover |
| 5 | 2 | Sanders / Smith | 4 | 6 | Banford / Orteig (Gelnaw) | Sanders / Smith | 7-6, 7-6 |
| 6 | 1 | Norton / Overacker | 5 | 7 | O'Neil / Williamson | Norton / Overacker | default |
| 6 | 2 | Thomson / Tucker | 5 | 6 | Mitchell / Warren | Thomson / Tucker | 6-4, 6-1 |
| 7 | 1 | Reilly / Tatum | 6 | 7 | Goodwin / Prescott | Reilly / Tatum | 6-2, 6-1 |
| 7 | 2 | Dynan / Ho | 6 | 6 | Hayes / Sorensen | Hayes / Sorensen | 6-2, 6-2 |
| W2 | 1 | Frieders / Sadowski | W1 | 7 | Graham / Reagan | Frieders / Sadowski | 6-4, 6-1 |
| W2 | 2 | Aleardi / Kay | W1 | 6 | Norley / Ruggieri | Aleardi / Kay | 6-2, 6-0 |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 6 | Augustine / Johnson lost to Morse / Russo to finish 6th |
| 2 | 2 | Fox / Kloud defeated Connell / Peloso to finish 2nd |
| 2 | 6 | Sibbett / Wheeler lost to Hanratti / Imbruce to finish 6th |
| 3 | 2 | Ahrens / Grillo defeated Heron / Parrott to finish 2nd |
| 3 | 6 | Beecher / Hladick and Burns / John did not play each other |
| Beecher / Hladick finished 6th behind Burns / John based upon games won (21-45) | ||
| 4 | 2 | Corcoran / Dunn defeated Schmitz / Walker to finish 2nd |
| 5 | 1 | Dial / Radecki defeated Sanders / Smith to finish 1st |
| 5 | 2 | Sanders / Smith lost to Dial / Radecki to finish 2nd |
| 7 | 2 | In a three-way tie between Dynan / Ho, Laska / Mitchell and Lindberg / Nelson |
| Dynan / Ho beat both opponents to finish 2nd | ||
| Lindberg / Nelson defeated Laska / Mitchell to finish 3rd |