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 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | McGoldrick / Patch | 1 | 7 | Kaye / Turk | Kaye / Turk | 6-4, 6-3 |
| 2 | 2 | Shen / Yee | 1 | 6 | Stevenson / Toft-Nielsen | Stevenson / Toft-Nielsen | 6-1, 6-2 |
| 3 | 1 | Gesing / Van Ess | 2 | 8 | Mierendorf / Rwambuya | Gesing / Van Ess | walk over |
| 3 | 2 | Grzymski / John | 2 | 7 | Cooney / Owsley | Cooney / Owsley | 6-3, 6-3 |
| 4 | 1 | Orteig / Regan | 3 | 7 | Eccleston / Scanlon | Orteig / Regan | walk over |
| 4 | 2 | Hanrattie / Imbruce | 3 | 6 | Hriston-Zech / Johnson | Hanrattie / Imbruce | 7-5, 6-4 |
| 5 | 1 | DiCapua / McDaniel | 4 | 8 | Glenaw / Posner | DiCapua / McDaniel | 6-2, 7-6 |
| 5 | 2 | Beecher / Hladick | 4 | 7 | Karr / Trager | Karr / Trager | 6-7, 6-2, 6-1 |
| 6 | 1 | Fox / Pine | 5 | 7 | Motherway / Root | Fox / Pine | walk over |
| 6 | 2 | Gaeta / Van der Loo | 5 | 6 | Siegel / Swift | Gaeta / Van der Loo | 6-1, 6-1 |
| 7 | 1 | Burkhart / McCarthy | 6 | 7 | Pierce / Scerbo | Burkhart / McCarthy | 6-0, 6-0 |
| 7 | 2 | Connell / Peloso | 6 | 6 | Finnigan / Wise | ||
| 8 | 1 | Root / Tierney | 7 | 7 | Franz / Kerridge | Root / Tierney | walk over |
| 8 | 2 | Markin / Prior | 7 | 6 | Mijne / Woods | Markin / Prior | default |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 6 | Stevenson / Toft-Nielsen lost to DiRubio / Ondash to finish 6th |
| 2 | 2 | Shen / Yee defeated Crigler / Kolb to finish 2nd |
| 3 | 2 | Grzymski / John defeated Baldwin / Laughton to finish 2nd |
| 4 | 7 | In a 3-way tie, Karr / Trager lost to both Raneri / Watt and Brill / Sullivan to finish 7th |
| 5 | 2 | Beecher / Hladick defeated Prochilo / Russo to finish 2nd |
| 5 | 6 | Burnaman / Buttrick did not play Siegel / Swift, so the 3rd tiebreaker is in effect |
| Burnaman / Buttrick won more total games (41) than Siegel / Swift (39), so Siegel / Swift finishes 6th | ||
| 6 | 2 | Gaeta / Van der Loo defeated Clarke / De Kanter to finish 2nd |
| 8 | 2 | In a 3-way tie, Kazlauskus / Knight lost to both Markin / Prior and Sibbett / Wheeler to finish 4th |
| Markin / Prior and Sibbett / Wheeler did not play each other, so the 3rd tiebreaker is in effect | ||
| Markin / Prior won more games (56) than Sibbett / Wheeler (53) to finish 2nd |