This prestigious award is given to that participant who achieves the lowest score, or as the award states, for “Horrendously Bad Guessing.” The winner is given a free entry in the following year’s competition. Christened in 1996, the award is so named in honor of the immortal Brandy Stout, who scored what is believed to be an unattainable score of 30 points. To achieve this ignominious feat, Brandy somehow managed to pick only 12 of the first 32 games correctly, 2 in the second round and was completely out of the competition by the time the Sweet Sixteen teams were established. According to crack mathematician, Numlock Salmon, the odds of achieving a score this low are 3.2 million to one.
| YEAR | WINNER | POINTS |
|---|---|---|
| 2025 | Tom Roche (The first five-time “winner”) | 69 |
| 2024 | Tom Roche (The first four-time “winner”) | 59 |
| 2023 | Jeff Baum | 49 |
| 2022 | Tom Roche (The first three-time “winner”) | 54 |
| 2021 | Maluri Fernandez | 47 |
| 2020 | Pandemic – No Tournament | — |
| 2019 | Sonia Tripolitano | 44 |
| 2018 | Gerald Eggink (Also the 2019 Overall Winner) | 60 |
| 2017 | Ron Cushing (Also the 2012 Overall Winner) | 76 |
| 2016 | David Ditlevsen | 35 |
| 2015 | David Ditlevsen | 76 |
| 2014 | David Ditlevsen | 57 |
| 2013 | Bill Levitan | 61 |
| 2012 | David Ditlevsen | 64 |
| 2011 | Wen Tong | 33 |
| 2010 | Robert Sheppard | 58 |
| 2009 | Gordon Bjorkman III | 65 |
| 2008 | Donna Riley | 70 |
| 2007 | Derek Maruyama | 79 |
| 2006 | Ali “Bud” Linder | 53 |
| 2005 | William LeBoeuf | 21* |
| 2004 | Shelly Smith | 39 |
| 2003 | Brandy Stout ?!?! | 38 |
| 2002 | Karen Taylor | 46 |
| 2001 | Tom Roche | 54 |
| 2000 | Tom Roche | 54 |
| 1999 | Karen Taylor | 65 |
| 1998 | Bill “Random” Malloch | 45 |
| 1997 | Michael Coyne | 79 |
| 1996 | Brandy Stout (Award is given its current name, “The Brandy Award”) | 30 |
| 1995 | Nina Bonds (Remarkably attains both the highest overall score and the lowest) | Lost to antiquity |
*Believed to be intentional