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| Top 50 Players Winter of Our Discontent Challenge December 1999–January 2000 |
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| Rank | Handicapper | Wins/Races | Profit or Loss |
| 1 | handi-crapper | 5/15 | $143.40 |
| 2 | snakes pit | 4/15 | $137.20 |
| 3 | Gigi | 3/12 | $130.30 |
| 4 | chunky | 2/4 | $117.70 |
| 5 | Christian | 3/11 | $108.20 |
| 6 | Bricary | 1/7 | $107.20 |
| 7 | brenner | 1/8 | $105.20 |
| 8 | cooker | 2/15 | $95.40 |
| 9 | RALPH | 2/15 | $56.90 |
| 10 | RON PECK | 1/13 | $56.40 |
| 11 | michael | 2/7 | $54.60 |
| 12 | THEDUKE | 1/5 | $40.60 |
| 13 | Christopher Olson | 2/8 | $39.10 |
| 14 | oddson | 2/8 | $39.10 |
| 15 | cowgirl | 3/15 | $38.00 |
| 16 | BLONDE FILLY | 1/7 | $36.60 |
| 17 | Marcia | 5/15 | $35.60 |
| 18 | d revels | 4/10 | $30.10 |
| 19 | psreg | 4/14 | $29.00 |
| 20 | Tout | 3/10 | $28.80 |
| 21 | elmley | 3/5 | $27.60 |
| 22 | jerry | 1/12 | $26.60 |
| 23 | Frank Seitz | 3/10 | $24.00 |
| 24 | shark | 1/14 | $22.60 |
| 25 | PIE | 4/14 | $22.30 |
| 26 | annand | 5/13 | $21.90 |
| 27 | Fishman | 6/15 | $21.80 |
| 28 | gonkster | 3/14 | $17.90 |
| 29 | keyshaun | 3/5 | $16.70 |
| 30 | twodollarman | 3/15 | $16.20 |
| 31 | LDK | 4/14 | $13.40 |
| 32 | RJ Mack | 1/7 | $12.40 |
| 33 | 97ingenitoan | 3/9 | $12.20 |
| 34 | CLIFFC37 | 1/3 | $12.00 |
| 35 | jampru57 | 4/15 | $11.90 |
| 36 | DARKHORSE | 2/15 | $11.40 |
| 37 | RDP42 | 1/1 | $10.80 |
| 38 | Super T | 1/1 | $10.80 |
| 39 | John Walden | 1/8 | $10.40 |
| 40 | baggypants | 1/4 | $10.00 |
| 41 | mark o`brien | 1/4 | $10.00 |
| 42 | moonbud | 2/4 | $9.40 |
| 43 | 7250rich | 3/14 | $9.00 |
| 44 | Dick's Pick's | 1/2 | $9.00 |
| 45 | johnnyuma | 1/2 | $8.80 |
| 46 | Pick3 | 1/2 | $8.80 |
| 47 | rolo racer | 1/2 | $8.80 |
| 48 | Turkoman | 2/12 | $8.80 |
| 49 | pcalloway | 1/10 | $8.60 |
| 50 | crisco | 3/12 | $8.00 |
| 51 | Don B. | 1/5 | $8.00 |
| 52 | bigvinnie | 3/7 | $7.90 |
| 53 | Czar | 3/7 | $7.90 |
| 54 | thebdstsob | 2/5 | $7.70 |
| 55 | cougfan300 | 1/3 | $6.80 |
| 56 | Equitrak | 1/3 | $6.80 |
| 57 | loki | 2/12 | $6.80 |
| 58 | rico | 1/3 | $6.80 |
| 59 | burgerbaron | 1/11 | $6.60 |
| 60 | texas6pack | 5/13 | $6.30 |
| 61 | TheEdge | 2/8 | $6.20 |
| 62 | Julian The Apostate | 1/6 | $6.00 |
| 63 | olyaie | 2/6 | $5.70 |
| 64 | edeg | 11/15 | $5.40 |
| 65 | ruffian | 3/9 | $5.40 |
| 66 | Joeaveragefan | 2/6 | $5.20 |
| 67 | fasthorsie | 3/11 | $5.10 |
| 68 | CLOVERLYSPORTS | 2/14 | $5.00 |
| 69 | Gary Mc | 2/9 | $4.60 |
| 70 | krenny | 2/13 | $4.60 |
| 71 | LEON CASSELL | 1/11 | $4.40 |
| 72 | kyle123 | 2/11 | $4.00 |
| 73 | scrndoor | 3/13 | $4.00 |
| 74 | sack | 2/7 | $3.70 |
| 75 | Mike Bollinger | 4/14 | $3.50 |
| 76 | DOMAS | 2/7 | $3.40 |
| 77 | ribot | 3/9 | $3.40 |
| 78 | brlow | 1/5 | $3.20 |
| 79 | bd4229 | 2/8 | $3.00 |
| 80 | dpimmel | 1/5 | $3.00 |
| 81 | Chuck | 2/3 | $2.70 |
| 82 | IR8 | 2/3 | $2.70 |
| 83 | mopiey | 2/3 | $2.70 |
| 84 | ebarraza | 1/1 | $2.50 |
| 85 | fred baker | 1/1 | $2.50 |
| 86 | rocky | 2/10 | $2.20 |
| 87 | Flats | 2/8 | $1.70 |
| 88 | francis s. | 3/11 | $1.60 |
| 89 | Ozzy | 5/12 | $1.50 |
| 90 | mikemelt | 3/11 | $1.40 |
| 91 | tarmstro | 2/9 | $1.00 |
| 92 | petwong | 1/6 | $0.80 |
| 93 | Sircapperr | 2/15 | $0.80 |
| 94 | Jasen | 1/2 | $0.50 |
| 95 | mojambo2 | 4/13 | $0.50 |
| 96 | Moses | 1/2 | $0.50 |
| 97 | Robert M | 3/15 | $0.50 |
| 98 | radar | 1/13 | $0.40 |
| 99 | DBonds | 1/2 | $0.20 |
| 100 | 1 | 0/0 | $0.00 |
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