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 |
2015 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Gould / Gould | 1 | 7 | Burr / Minter | Gould / Gould | walkover |
| 2 | 2 | Eccleston / Scanlon | 1 | 6 | McGoldrick / Stevenson | ||
| 3 | 1 | Prochilo / Shonfield | 2 | 7 | Baldwin / Laughton | Prochilo / Shonfield | 6-2, 3-6, 7-5 |
| 3 | 2 | Fox / Pine | 2 | 6 | Morse / Russo | Fox / Pine | 6-1, 7-6 |
| 4 | 1 | Burkhart / McCarthy | 3 | 8 | DiCapua / McDaniel | ||
| 4 | 2 | Blair / Fuller | 3 | 7 | Karr / Trager | Blair / Fuller | 6-0, 6-0 |
| 5 | 1 | Etergino / Wilson | 4 | 8 | Lydon / Murphy | Etergino / Wilson | walkover |
| 5 | 2 | Sibbett / Wheeler | 4 | 7 | O'Neil / Williamson | Sibbett / Wheeler | 6-1, 6-0 |
| 6 | 1 | Mohr / Murphy | 5 | 7 | Harris / Mehos | Mohr / Murphy | default |
| 6 | 2 | Root / Tierney | 5 | 6 | Corcoran / Dunn | Root / Tierney | 6-1, 6-3 |
| 7 | 1 | Gilbert / Perkins | 6 | 8 | Markin / Prior | Gilbert / Perkins | default |
| 7 | 2 | Harmon / Mahoney | 6 | 7 | Mazabras / Murray | Harmon / Mahoney | default |
Teams highlighted in yellow above are teams involved in ties, see explanations below
Teams highlighted in blue above have forfeited their challenge due to Membership Requirements not being met
| Flight | Pos | Notes |
| 2 | 2 | Eccleston / Scanlon defeated Gesing / Van Ess to finish 2nd |
| 3 | 7 | Karr / Trager lost to Burnaman / Buttrick to finish 7th |
| 4 | 2 | Blair / Fuller defeated Hriston-Zech / Penman to finish 2nd |
| 4 | 7 | Brill / Sullivan and O'Neil / Williamson finished tied through all 3 tiebreakers |
| Brill / Sullivan won the coin toss, so O'Neil / Williamson finished 7th | ||
| 5 | 1 | Etergino / Wilson defeated Sibbett / Wheeler to finish 1st |
| 5 | 2 | Sibbett / Wheeler lost to Etergino / Wilson to finish 2nd |
| 5 | 6 | Corcoran / Dunn lost to Gillen / Haussler to finish 6th |
| 7 | 1 | Gilbert / Perkins defeated Harmon / Mahoney to finish 1st |
| 7 | 2 | Harmon / Mahoney lost to Gilbert / Perkins to finish 2nd |