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 |
2019 Winter Challenge Results
| Flight | Pos | Challenger | Flight | Pos | Challengee | Winner | Score |
| 2 | 1 | Reilly / Tatum | 1 | 6 | Fox / Kloud | Reilly / Tatum | 6-4, 7-6 |
| 2 | 2 | Sibbett / Wheeler | 1 | 5 | Morse / Russo | Morse / Russo | 6-4, 6-7, 6-4 |
| 3 | 1 | Laska / Mitchell | 2 | 6 | Blair / Warner | Laska / Mitchell | 6-0, 6-1 |
| 3 | 2 | Nelson / Yao | 2 | 5 | Augustine / Johnson | Nelson / Yao | 6-1, 6-4 |
| 4 | 1 | Street / Waldron | 3 | 7 | Eccleston / Gelnaw | Street / Waldron | 6-3, 6-4 |
| 4 | 2 | Bennett / Kaufman | 3 | 6 | John / Leverone | Bennett / Kaufman | 6-1, 3-6, 6-1 |
| 5 | 1 | Dinger / Simpson | 4 | 7 | Beecher / Hladick | Dinger / Simpson | 6-3, 6-0 |
| 5 | 2 | Parija / Pinchin | 4 | 6 | Discenza / Hott | Parija / Pinchin | 6-4, 1-6, 6-3 |
| 6 | 1 | Orteig / Prazenka | 5 | 7 | McKeever / Trager | Orteig / Prazenka | 6-3, 6-1 |
| 6 | 2 | Huang / Wang | 5 | 6 | Hetherington / Koller | Huang / Wang | 6-3, 6-1 |
| 7 | 1 | Brennan / Dunlop | 6 | 7 | Thomas / Vermeer | ||
| 7 | 2 | Gilio / LaShelle | 6 | 6 | Sparico / Turner | ||
| 8 | 1 | Fusco / Roomet | 7 | 6 | Dathan / Potter | Fusco / Roomet | 6-1, 6-0 |
| 8 | 2 | Forrest / Hanno | 7 | 5 | Pal / Siegel | Forrest / Hanno | 7-5, 3-6, 6-3 |
| W2 | 1 | Hennessy / Proctor | W1 | 5 | Graham / Reagan | Hennessy / Proctor | 7-6, 3-6, 6-4 |
| W2 | 2 | Maijala / Parrett | W1 | 4 | Norley / Ruggieri |
Teams highlighted in yellow above are teams involved in ties, see explanations below
| Flight | Pos | Notes |
| 1 | 5 | In a 3-way tie, Morse / Russo lost to both Bergman / Imbruce and Van Ess / Wietfeldt to finish 5th |
| 2 | 2 | Sibbett / Wheeler defeated Schmitz / Walker to finish 2nd |
| 2 | 5 | Augustine / Johnson defeated Blair / Warner to finish 5th |
| 2 | 6 | Blair / Warner lost to Augustine / Johnson to finish 6th |
| 3 | 1 | Laska / Mitchell defeated Nelson / Yao to finish 1st |
| 3 | 2 | Nelson / Yao losted to Laska / Mitchell to finish 2nd |
| 4 | 6 | Discenza / Hott lost to Sanders / Smith to finish 6th |
| 5 | 6 | In a 3-way tie, Hetherington / Koller lost to both Altieri / Frederico and Barton / Carlberg to finish 6th |
| 6 | 6 | Sparico / Turner and Thomas / Vermeer did not play each other, so we go to the 4th tiebreaker |
| Sparico / Turner won more games (36) than Thomas / Vermeer (30) to finsh 6th | ||
| 6 | 7 | Thomas / Vermeer (30) won fewer games than Sparico / Turner (36) to finsh 7th |
| 7 | 5 | Pal / Siegel lost to Frick / Rogers to finish 5th |
| W1 | 4 | Norley / Ruggieri defeated Graham / Reagan to finish 4th |
| W1 | 5 | Graham / Reagan lost to Norley / Ruggieri to finish 5th |
| W2 | 2 | Maijala / Parrett and Johnson / Noell did not play each other, so we go to the 4th tiebreaker |
| Maijala / Parrett won more games (23) than Johnson / Noell (19) to finish 2nd |