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 |
2008 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Duhamel / Gardner | 1 | 8 | Eydt / Laverack | Duhamel / Gardner | 6-3, 6-3 |
| 2 | 2 | Hays / Hood | 1 | 7 | Stewart / Teitler | ||
| 3 | 1 | Burger / O'Mahony | 2 | 8 | BYE | Burger / O'Mahony | walk over |
| 3 | 2 | Herbert / Himmel | 2 | 7 | Kaye / Turk | Herbert / Himmel | 6-0, 4-6, 6-3 |
| 4 | 1 | King / Loomis | 3 | 8 | BYE | King / Loomis | walk over |
| 4 | 2 | Nagle / Schwarz | 3 | 7 | Depuy / Ferraro | Nagle / Schwarz | 6-2, 6-2 |
| 5 | 1 | Dayton / Mylod | 4 | 8 | Czech / Stryker | Dayton / Mylod | default |
| 5 | 2 | Davis / Miller | 4 | 7 | Irwin / Slemp | Davis / Miller | default |
| 6 | 1 | Beusse / Reik | 5 | 8 | BYE | Beusse / Reik | walk over |
| 6 | 2 | DuPont / Manchuck | 5 | 7 | Licalzi / Truslow | DuPont / Manchuck | default |
| 7 | 1 | Engle / Niang | 6 | 8 | Gesing / Rigo | Engle / Niang | default |
| 7 | 2 | Schumacher / Watt | 6 | 7 | Barada / Kalal | Schumacher / Watt | 6-2, 6-3 |
| 8 | 1 | Augustine / Severance | 7 | 8 | Gardiner / Sotirhos | Augustine / Severance | default |
| 8 | 2 | Fannon / Thompson | 7 | 7 | Swanberg / Taddonio | ||
| 9 | 1 | Burns / Roscoe | 8 | 8 | BYE | Burns / Roscoe | walk over |
| 9 | 2 | Connelly / O’Dea | 8 | 7 | Cieszko / Todd | ||
| 10 | 1 | Capone / Moore | 9 | 8 | Gervase / Karr | Capone / Moore | default |
| 10 | 2 | Stevenson / Wood | 9 | 7 | Bauld / Mennitt | Stevenson / Wood | 6-0, 6-0 |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 7 | Stewart / Teitler lost to Purdy / Wrenn to finish 7th |
| 2 | 2 | Hays / Hood in a 3-way tie, won both matches vs the other 2 to finish 2nd |
| 5 | 2 | Davis / Miller beat Barrett / Watson to finish 2nd |
| 6 | 2 | DuPont / Manchuck in a 4-way tie (wow), went 2-1 vs the other 3 to tie for the top spot |
| In the next tie-breaker, they beat the other 2-1 team (Boeschenstein / Bright) to finish 2nd | ||
| 7 | 2 | Schumacher / Watt beat Appel / DeMarino to finish 2nd |
| 8 | 2 | Fannon / Thompson in a 4-way tie (wow again), went 3-0 vs the other 3 to finish 2nd |
| 9 | 1 | Burns / Roscoe beat Connelly / O’Dea to finish 1st |
| 9 | 2 | Connelly / O’Dea lost to Burns / Roscoe to finish 2nd |