The Mt Washington road race has given away a grand total of $178,895 since first awarding Gary Crossan $100 for setting a course record in 1984. Here are the top 100 (of 238) prize money winners.
| Top Prize money winners | |
| Rank | Name | | Amount | Times winning $ | Average won |
| 1 | Craig | Fram | $ 10,700.00 | 9 | $ 1,188.89 |
| 2 | Simon | Gutierrez | $ 8,000.00 | 12 | $ 666.67 |
| 3 | Dave | Dunham | $ 7,550.00 | 20 | $ 377.50 |
| 4 | Shewarge | Amare | $ 7,000.00 | 1 | $ 7,000.00 |
| 5 | Jonathan | Wyatt | $ 7,000.00 | 2 | $ 3,500.00 |
| 6 | Anna | Pirchtova | $ 6,850.00 | 7 | $ 978.57 |
| 7 | Matt | Carpenter | $ 5,650.00 | 5 | $ 1,130.00 |
| 8 | Jacqueline | Gareau | $ 5,250.00 | 10 | $ 525.00 |
| 9 | Brandy | Erholtz | $ 5,000.00 | 5 | $ 1,000.00 |
| 10 | Eric | Blake | $ 4,900.00 | 7 | $ 700.00 |
| 11 | Laura | Haefeli | $ 4,766.67 | 4 | $ 1,191.67 |
| 12 | Daniel | Kihara | $ 4,600.00 | 4 | $ 1,150.00 |
| 13 | Nicole | Hunt | $ 4,500.00 | 3 | $ 1,500.00 |
| 14 | Eric | Morse | $ 4,200.00 | 14 | $ 300.00 |
| 15 | Rickey | Gates | $ 4,100.00 | 6 | $ 683.33 |
| 16 | Derek | Froude | $ 3,800.00 | 3 | $ 1,266.67 |
| 17 | J'Ne | Day-Lucore | $ 3,200.00 | 5 | $ 640.00 |
| 18 | Julie | Peterson | $ 2,675.00 | 7 | $ 382.14 |
| 19 | Kim | Dobson | $ 2,500.00 | 2 | $ 1,250.00 |
| 20 | Paul | Low | $ 2,500.00 | 5 | $ 500.00 |
| 21 | Joan | Benoit-Samuelson | $ 2,000.00 | 2 | $ 1,000.00 |
| 22 | Joseph | Gray | $ 2,000.00 | 4 | $ 500.00 |
| 23 | Chris | Siemers | $ 2,000.00 | 1 | $ 2,000.00 |
| 24 | Magdellena | Thorsell | $ 1,750.00 | 1 | $ 1,750.00 |
| 25 | Sumner | Brown | $ 1,620.00 | 13 | $ 124.62 |
| 26 | Kasie | Enman | $ 1,600.00 | 4 | $ 400.00 |
| 27 | Sage | Canaday | $ 1,500.00 | 1 | $ 1,500.00 |
| 28 | Melissa | Moon | $ 1,500.00 | 1 | $ 1,500.00 |
| 29 | Cathy | Pearce | $ 1,500.00 | 4 | $ 375.00 |
| 30 | Kristin | Price | $ 1,500.00 | 1 | $ 1,500.00 |
| 31 | Chris | Maisto | $ 1,483.33 | 4 | $ 370.83 |
| 32 | Peg | Donovan | $ 1,433.33 | 5 | $ 286.67 |
| 33 | Bob | Hodge | $ 1,400.00 | 6 | $ 233.33 |
| 34 | Keith | Woodward | $ 1,360.00 | 13 | $ 104.62 |
| 35 | Suzy | West | $ 1,216.67 | 6 | $ 202.78 |
| 36 | Rebecca | Stockdale-Woolley | $ 1,216.66 | 6 | $ 202.78 |
| 37 | Tommy | Manning | $ 1,200.00 | 3 | $ 400.00 |
| 38 | Barbara | Remmers | $ 1,050.00 | 2 | $ 525.00 |
| 39 | Alice | Muriithi | $ 950.00 | 2 | $ 475.00 |
| 40 | Cathy | O'Brien | $ 950.00 | 2 | $ 475.00 |
| 41 | Mike | Casner | $ 900.00 | 7 | $ 128.57 |
| 42 | Dan | Verrington | $ 850.00 | 8 | $ 106.25 |
| 43 | Donna | Smyers | $ 808.33 | 6 | $ 134.72 |
| 44 | Andy | Ames | $ 800.00 | 4 | $ 200.00 |
| 45 | Pam | Moore | $ 800.00 | 2 | $ 400.00 |
| 46 | Carrie | Parsi | $ 800.00 | 7 | $ 114.29 |
| 47 | Martha | Rockwell | $ 770.00 | 4 | $ 192.50 |
| 48 | Sean | Hanley | $ 750.00 | 1 | $ 750.00 |
| 49 | Alayne | Adams | $ 700.00 | 2 | $ 350.00 |
| 50 | Alison | Bryant | $ 700.00 | 3 | $ 233.33 |
| 51 | Tara | Cardi | $ 700.00 | 1 | $ 700.00 |
| 52 | Nikki | Kimball | $ 700.00 | 2 | $ 350.00 |
| 53 | Neji | Makhlouf | $ 700.00 | 2 | $ 350.00 |
| 54 | Gideon | Mutisaya | $ 700.00 | 1 | $ 700.00 |
| 55 | Sandra | Natal | $ 700.00 | 2 | $ 350.00 |
| 56 | Chuck | Smead | $ 675.00 | 3 | $ 225.00 |
| 57 | Lisa | Goldsmith | $ 666.67 | 3 | $ 222.22 |
| 58 | Lynn | Brown | $ 600.00 | 1 | $ 600.00 |
| 59 | Matthew | Byrne | $ 600.00 | 2 | $ 300.00 |
| 60 | Jennifer | Campbell | $ 600.00 | 2 | $ 300.00 |
| 61 | Max | King | $ 600.00 | 1 | $ 600.00 |
| 62 | Erica | Larson | $ 600.00 | 1 | $ 600.00 |
| 63 | Megan | Lund | $ 600.00 | 1 | $ 600.00 |
| 64 | Kevin | Tilton | $ 600.00 | 3 | $ 200.00 |
| 65 | Louise | Voghel | $ 600.00 | 3 | $ 200.00 |
| 66 | Clint | Wells | $ 600.00 | 1 | $ 600.00 |
| 67 | Tom | Borschell | $ 550.00 | 2 | $ 275.00 |
| 68 | Julie | White | $ 550.00 | 2 | $ 275.00 |
| 69 | Louis | Dunlap | $ 508.33 | 4 | $ 127.08 |
| 70 | Janine | Aiello | $ 500.00 | 1 | $ 500.00 |
| 71 | Tom | Carroll | $ 500.00 | 3 | $ 166.67 |
| 72 | Amber | Ferreira | $ 500.00 | 1 | $ 500.00 |
| 73 | Liz | Kellogg | $ 500.00 | 3 | $ 166.67 |
| 74 | Joseph | Kibor | $ 500.00 | 1 | $ 500.00 |
| 75 | Sue | LaChance | $ 500.00 | 3 | $ 166.67 |
| 76 | Anita | Ortiz | $ 500.00 | 1 | $ 500.00 |
| 77 | Glenn | Randall | $ 500.00 | 2 | $ 250.00 |
| 78 | Tatiana | Titova | $ 500.00 | 1 | $ 500.00 |
| 79 | Gary | Crossan | $ 450.00 | 2 | $ 225.00 |
| 80 | Liza | Grudzinski | $ 400.00 | 1 | $ 400.00 |
| 81 | Kelli | Lusk | $ 400.00 | 2 | $ 200.00 |
| 82 | Matt | Russell | $ 400.00 | 1 | $ 400.00 |
| 83 | Margo | Webber | $ 400.00 | 1 | $ 400.00 |
| 84 | Christine | Lundy | $ 366.66 | 1 | $ 366.66 |
| 85 | Kelly | Brinkeman | $ 350.00 | 1 | $ 350.00 |
| 86 | Francis | Burdett | $ 350.00 | 4 | $ 87.50 |
| 87 | Robert | Ratcliffe | $ 350.00 | 4 | $ 87.50 |
| 88 | Brian | Reinhold | $ 325.00 | 2 | $ 162.50 |
| 89 | Richard | Bolt | $ 300.00 | 2 | $ 150.00 |
| 90 | Anna | Brook | $ 300.00 | 1 | $ 300.00 |
| 91 | Kari | Distefano | $ 300.00 | 1 | $ 300.00 |
| 92 | Barbara | Higgins-Nelson | $ 300.00 | 1 | $ 300.00 |
| 93 | Abraham | Limo | $ 300.00 | 1 | $ 300.00 |
| 94 | Chris | Lundstrom | $ 300.00 | 1 | $ 300.00 |
| 95 | Amber | Moran | $ 300.00 | 1 | $ 300.00 |
| 96 | Guy | Stearns | $ 300.00 | 1 | $ 300.00 |
| 97 | Dorcas | Wonsavage | $ 266.67 | 2 | $ 133.34 |
| 98 | Bruce | Bridgham | $ 250.00 | 2 | $ 125.00 |
| 99 | Ruth | Hall | $ 250.00 | 1 | $ 250.00 |
| 100 | Jay | Johnson | $ 250.00 | 1 | $ 250.00 |
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