| Year | Aussie Open | French Open | Wimbledon | US Open | Year-end #1 |
| 1995 | Jay | ??? | |||
| 1996 | Jimbo | ??? | |||
| 1997 | Tina | Tina | Tina | ||
| 1998 | Kyle | Thad | Kyle | Steve | Kyle |
| 1999 | Not Contested | Rick | Barry | Steve | Jay |
| 2000 | Kyle | Brooke | Brooke | DanP | Thad |
| 2001 | David | Thad | Brooke | Brooke | Brooke |
| 2002 | Chief | Rick | Wagner | Jean | Brooke & Jay |
| 2003 | Jay | Kyle | Chief | Jay | Jay |
| 2004 | David | Jay | David | Wagner | Wagner |
| 2005 | Jay | NJampol | David | NJampol | DrDan & Jay |
| 2006 | Keith | Judge | Rickoxo | David | Rickoxo |
| 2007 | David | Barry | Barry | Jay | Barry |
| 2008 | David | Judge | Brooke | DanP | DanP & Eric |
| 2009 | Rick | Derek | Jay | Rickoxo | Rick |
| 2010 | Brooke | Derek | Brooke | Barry | Brooke |
| 2011 | DanP | Chief | Barry | Kraken | Kraken |
| 2012 | Chief | Rick | Judge | Wagner | Rickoxo |
| 2013 | Jean | Brooke | Kraken | Jean | Kraken |
| 2014 | Judge | Sangmin | Brooke | Jean | Judge |
| 2015 | Judge | Jean | Paul | Jean | Paul |
| 2016 | DanP | Brooke | Jean | Jay | Brooke |
| 2017 | Jay | Rick | Chief | Barry | Chief |
| 2018 | Chief | Kraken | Kraken | Shoe | Kraken |
| 2019 | Shoe | Max | Shoe | Barry | Shoe |
| 2020 | SteveB | Shoe | N/A | Brooke | Jay & SteveB |
| 2021 | DanP | Chief | Shoe | Brooke | Chief |
| 2022 | SteveB | Brooke | Chief | Eric | DanP |
| 2023 | Shoe | Eric | Jay | Jay | DanP |
| 2024 | Jay | Mo | Chief | Wagner | Kraken |
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