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 |
2014 Fall Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Donovan / Leddy | 1 | 7 | Loomis / Pellegrino | ||
| 2 | 2 | Gesing / Van Ess | 1 | 6 | Shen / Yee | Shen / Yee | 2-6, 7-5, 6-1 |
| 3 | 1 | Eccleston / Scanlon | 2 | 7 | Morse / Russo | Eccleston / Scanlon | 6-1, 6-4 |
| 3 | 2 | Augustine / Johnson | 2 | 6 | Heron / Parrott | ||
| 4 | 1 | Fox / Pine | 3 | 7 | Hanrattie / Imbruce | Fox / Pine | walk over |
| 4 | 2 | Gelnaw / Posner | 3 | 6 | Gaeta / Kanter | ||
| 5 | 1 | Prochilo / Shonfield | 4 | 7 | DeMayo / Gervase | Prochilo / Shonfield | default |
| 5 | 2 | Connell / Peloso | 4 | 6 | Brill / Sullivan | Connell / Peloso | 6-2, 6-0 |
| 6 | 1 | Sibbett / Wheeler | 5 | 7 | Banford / Dial | Banford / Dial | 6-2, 6-3 |
| 6 | 2 | Ognibene / Pertuiello | 5 | 6 | Siegel / Swift | ||
| 7 | 1 | Etergino / Wilson | 6 | 8 | Markin / Prior | ||
| 7 | 2 | Gillen / Haussler | 6 | 7 | Mijne / Woods | ||
| 8 | 1 | Blair / Fuller | 7 | 8 | Patterson / Slatoff | Blair / Fuller | 6-0, 6-0 |
| 8 | 2 | Mohr / Murphy | 7 | 7 | Cox / Marchiony | Mohr / Murphy | 6-0, 6-2 |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 6 | Burr / Minter and Shen / Yee did not play each other |
| Burr / Minter finished ahead of Shen / Yee (6th) based on games won (36-35) | ||
| 2 | 6 | Heron / Parrott lost to Gould / Gould to finish 6th |
| 3 | 2 | Augustine / Johnson defeated Casey / Prazenka to finish 2nd |
| 4 | 2 | Gelnaw / Posner defeated Beecher / Hladick to finish 2nd |
| 5 | 1 | Prochilo / Shonfield defeated Connell / Peloso to finish 1st |
| 5 | 2 | Connell / Peloso lost to Prochilo / Shonfield finish 2nd |
| 6 | 1 | Sibbett / Wheeler defeated Ognibene / Pertuiello to finish 1st |
| 6 | 2 | Ognibene / Pertuiello lost to Sibbett / Wheeler to finish 2nd |
| 7 | 2 | Gillen / Haussler defeated Schmitz / Walker to finish 2nd |
| 7 | 7 | Mazabras / Murray and Cox / Marchiony did not play each other |
| Mazabras / Murray finished ahead of Cox / Marchiony (7th) based on games won (30-26) |