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 |
2021 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Hott / Wallace | 1 | 7 | Deligtisch / Stallings | Hott / Wallace | Default |
| 2 | 2 | Sibbett / Wheeler | 1 | 6 | Bennett / Kaufman | Bennett / Kaufman | 1-6, 6-2, 6-1 |
| 3 | 1 | Ahrens / Castiglione | 2 | 6 | Eccleston / Scanlon | Ahrens / Castiglione | Default |
| 3 | 2 | Huang / Wang | 2 | 5 | Sigg / Van Ess | Sigg / Van Ess | 6-3, 6-1 |
| 4 | 1 | Gilbert / Segalas | 3 | 7 | Augustine / Gesing | Gilbert / Segalas | Default |
| 4 | 2 | Fewster / Hopkins | 3 | 6 | Orteig / Prazenka | Fewster / Hopkins | 6-2, 4-6, 7-5 |
| 5 | 1 | Campo / Joyce | 4 | 6 | Benton / Prescott | Campo / Joyce | 6-2, 6-0 |
| 5 | 2 | Donovan / Maynard | 4 | 5 | Ladley / Wells | Donovan / Maynard | 6-1, 6-1 |
| 6 | 1 | Carr / Kerchoff | 5 | 7 | Fillingham / Goldenberg | Carr / Kerchoff | 6-1, 6-1 |
| 6 | 2 | Casey / McClave | 5 | 6 | Dathan / Potter | Casey / McClave | 6-3, 6-0 |
| W2 | 1 | Sousa / Stevenson | W1 | 8 | Ahrens / Grillo | Sousa / Stevenson | Default |
| W2 | 2 | Kupersmith / Willey | W1 | 7 | Brennan / Johnson | Brennan / Johnson | 3-6, 6-4, 6-3 |
| W3 | 1 | Norley / Ruggieri | W2 | 7 | Aleardi / Roddy | Aleardi / Roddy | 6-2, 6-2 |
| W3 | 2 | Balkun / Rashad | W2 | 6 | Hennessy / Proctor | Balkun / Rashad | Default |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 6 | In a 3-way tie, Bennett / Kaufman, Connell / Prochilo, each won 1 match against the other 2 |
| Next, Connell / Prochilo won 3 sets to finish 4th, while the only 2 teams only won 2 sets | ||
| Finally, Bennett / Kaufman lost to Foley / Yao to finish 6th | ||
| 4 | 5 | In a 3-way tie, Austin / Mason, Ladley / Wells, McKeever / Trager each won 1 match against the other 2 |
| Next, Austin / Mason and McKeever / Trager won 3 sets, while Ladley / Wells won 2 to finish 5th | ||
| 5 | 6 | Dathan / Potter and Ivanov / Quigley tied for 5th/6th, but didn't play each other, so we se the games won tiebreaker |
| Here Ivanov / Quigley won 39 games to finish 5th and Dathan / Potter won 27 games to finish 6th | ||
| W2 | 6 | In a 3-way tie between Casey / Guzzetti, Flynn / Frawley, Hennessy / Proctor, not all matches were played |
| Casey / Guzzetti and Hennessy / Proctor did not play each other | ||
| Casey / Guzzetti and Flynn / Frawley each won 1 match, while Hennessy / Proctor won 0 to finish 6th |