| Name | Winnings | Date(s) | Notes |
| Kevin Olmstead | $2,180,000 | 04/06-10/01 | Won $27,000 on "Jeopardy!"; Paul Dillon's PAF |
| Ed Toutant | $1,860,000 | 01/28-31/01, 09/07/01 | (see below); Kelly Buszek's PAF |
| John Carpenter | $1,125,000 | 11/18-19/99, 05/24-25/00 | Won $125,000 in TOC |
| Dan Blonsky | $1,000,500 | 01/16-18/00, 05/23/00 | Won $500 in TOC |
| Joe Trela | $1,000,500 | 03/23/00, 05/21/00 | Won $500 in TOC; Bill Harris' PAF |
| Bernie Cullen | $1,000,000 | 04/15/01 | Won $69,102 on "Jeopardy!" |
| David Goodman | $1,000,000 | 07/11/00 | David Hamilton's PAF |
| Bob House | $1,000,000 | 06/11-13/00 | |
| Kim Hunt | $1,000,000 | 06/18-07/06/00 | |
| Tim Shields | $516,000 | 01/14/00, 05/23-24/00 | (see below); Won $16,000 in TOC; Sister Juliet Shields' PAF |
| Michael Shutterly | $500,500 | 08/24-25/99, 05/24/00 | Won $500 in TOC; Won $49,200 on "Jeopardy!"; Stefany Needel's PAF |
| Mary Burke | $500,000 | 06/14/01 | |
| Moe Cain | $500,000 | 05/01/01 | |
| Justin Ray Castillo | $500,000 | 11/22-26/00 | |
| Rob Coughlin | $500,000 | 01/23/00 | |
| David Fite | $500,000 | 01/09-10/00 | |
| Gary Gambino | $500,000 | 03/01/01 | Won $1,000 on "Jeopardy!" |
| Phil Gibbons | $500,000 | 08/13-15/00 | |
| Stephanie Girardi | $500,000 | 02/15-17/00 | |
| Tom Hoobler | $500,000 | 06/03-05/01 | |
| Joe Kelleher | $500,000 | 07/23/00 | |
| Jim Matthews | $500,000 | 12/06/00 | |
| Rob & Mary Beth McNally | $500,000 | 05/17/01 | Couples Edition I |
| Mike Menz | $500,000 | 04/27/00 | |
| Tom O'Brien | $500,000 | 06/07-11/00 | Won $1,200 on "Jeopardy!" |
| Steve Perry | $500,000 | 04/22/01 | Matt Marcotte's, Timothy Sternberg's, and Beth Zoller's PAF |
| David Stewart | $500,000 | 04/01/01 | |
| Patricia Thompson | $500,000 | 11/08/00 | |
| David Forman | $375,000 | 02/24/00, 05/21/00 | Won $125,000 in TOC |
| Al Schaeffer | $312,500 | 03/14-16/00, 05/25/00 | Won $62,500 in TOC |
| Neil Larrimore | $282,000 | 11/24/99, 05/23/00 | Won $32,000 in TOC |
| Michael Avitzur | $266,000 | 02/15/00, 05/21-23/00 | Won $16,000 in TOC |
| Thomas Ashton | $250,500 | 04/13-16/00, 05/25/00 | Won $500 in TOC; Brother of Robert Ashton |
| Robert Toby Moore | $250,500 | 11/17-18/99, 05/25/00 | Won $500 in TOC; Blake Burton's PAF |
| Andy Aaron | $250,000 | 12/12-13/00 | Won $5,000+ on "The Big Showdown"; Husband of Jackie Aaron |
| Chris Barker | $250,000 | 04/23/00 | |
| Tom Bolton | $250,000 | 11/28-29/00 | |
| Peter Braxton | $250,000 | 02/08/01 | Won $33,402 on "Jeopardy!" |
| Eric Buske | $250,000 | 10/15/00 | |
| Gary Cahall | $250,000 | 03/27-29/01 | |
| Jane Charnin-Aker | $250,000 | 04/20-22/01 | |
| David Clayton | $250,000 | 12/13-20/01 | |
| Dave Colquitt | $250,000 | 10/29/00 | |
| Bob Combs | $250,000 | 04/29/01 | Won $22,701 on "Jeopardy!" |
| Dan Demars | $250,000 | 02/20/00 | |
| Jason Dickinson | $250,000 | 05/10/00 | |
| Aurko Dutta | $250,000 | 04/18-06/06/02 | |
| Adam Edgell | $250,000 | 04/27-29/01 | |
| Phil Gibson | $250,000 | 10/04-05/00 | |
| Eric Grosskurth | $250,000 | 02/15/01 | Phoned Bob Shore; Eddie Timanus' PAF |
| Chris Gum | $250,000 | 12/12/00 | |
| Dave Hann | $250,000 | 12/06/01 | |
| Allen Harris | $250,000 | 07/11/00 | |
| Terry Jones | $250,000 | 12/05/00 | |
| Ken Krantz | $250,000 | 04/24-26/01 | |
| Jim Lairmore | $250,000 | 07/18-20/00 | |
| Gary Levine | $250,000 | 11/11/99 | |
| Leo Luberecki | $250,000 | 06/06/02 | |
| Jonathan Lubin | $250,000 | 02/04/02 | College Week II |
| David MacLaine | $250,000 | 08/01-03/00 | |
| Tony Mangaser | $250,000 | 04/01-03/01 | |
| Matt Marcotte | $250,000 | 11/20/99 | Phoned Steve Perry |
| Jack Martin, Jr. | $250,000 | 01/17-18/01 | |
| Scott McKeeve | $250,000 | 10/04-11/01 | |
| John Norquist | $250,000 | 01/24/01 | Antoinette Powell's PAF |
| Eric Oberhand | $250,000 | 02/28/01 | |
| Reece O'Dell | $250,000 | 11/02/00 | |
| Henry Olsen | $250,000 | 04/03/01 | |
| Jeanne Pomenti | $250,000 | 04/26-27/01 | |
| Martin Poteralski | $250,000 | 04/30/00, 05/20-21/01 | Zero Winners Edition (missed Q5) |
| Nancy Amanda Redd | $250,000 | 02/04/02 | College Week II |
| Joel Reid | $250,000 | 12/14-17/00 | |
| Ian Reifowitz | $250,000 | 03/30-04/02/00 | |
| David Rice | $250,000 | 04/04-06/00 | |
| Robin Riglin | $250,000 | 10/05-08/00 | |
| Joe Roberts | $250,000 | 01/09/00 | |
| Christopher Ruth | $250,000 | 08/27-29/00 | Won $40,600+ on "Jeopardy!" |
| Marty Scott | $250,000 | 01/14/01 | Won $66,002 on "Jeopardy!" |
| Kevin Simcox | $250,000 | 03/09-12/00 | |
| Connie Stoltz | $250,000 | 02/15-16/01 | |
| Doug Van Gundy | $250,000 | 08/19-20/99 | Famous fiddler and writer |
| Donna White | $250,000 | 04/10-12/01 | |
| Paul Young | $250,000 | 09/07-12/00 | |
| Peter & Abby Abide | $125,000 | 11/24/00 | Family Edition |
| John Aducci | $125,000 | 06/06/00 | |
| Carol Alaimo | $125,000 | 06/27/02 | Final contestant |
| Alex Aldrich | $125,000 | 10/31/00 | |
| Kevin Baggett | $125,000 | 04/05/01 | |
| David Becker | $125,000 | 02/22/01 | Won $27,000+ on "Jeopardy!" |
| Rob Berman | $125,000 | 11/22/99 | |
| George Berwick | $125,000 | 03/07-28/02 | |
| Mike Billok | $125,000 | 03/16-19/00 | |
| Jason Block | $125,000 | 01/11-12/00 | Phoned Rick Grimes; Won $38,451 on "Jeopardy!" and $1,000 on "Catch 21" |
| Justin Bowers | $125,000 | 02/04-07/02 | College Week II |
| Mitch Brown | $125,000 | 03/04/01 | |
| Stephen Bryan & Elise Kavanaugh | $125,000 | 05/18/01 | Couples Edition I |
| Scott Camloh | $125,000 | 03/30-04/01/01 | |
| Charlie Carson | $125,000 | 05/01/01 | |
| Barry Chromey | $125,000 | 01/12-14/01 | |
| Steve Cornman | $125,000 | 08/01/00 | Judy Bartoletti's PAF |
| Tracy Cotter | $125,000 | 10/31/00 | |
| Jason Dettelbach | $125,000 | 01/18/00 | |
| Matthew & Jennifer Dooher | $125,000 | 02/14-28/02 | Couples Edition II |
| Eileen Duffy | $125,000 | 04/11-13/00 | |
| Steve Ellson | $125,000 | 02/10-13/00 | |
| Joe Erlanger | $125,000 | 04/20/01 | |
| Carlo Espinas | $125,000 | 09/27-10/04/01 | |
| Ali Fahmy & Laurel Podulke | $125,000 | 05/17-18/01 | Couples Edition I |
| Todd Flanders | $125,000 | 07/25-27/00 | |
| Steve Flynn | $125,000 | 02/18/01 | |
| Tony Frausto | $125,000 | 10/12/00 | |
| Roger Friedman | $125,000 | 08/16-19/01 | |
| Greg Gibbs | $125,000 | 03/08-09/01 | |
| Mark Gluckstern | $125,000 | 02/01-02/00 | |
| John Grochowski | $125,000 | 07/25/00 | |
| Archie Harris | $125,000 | 10/18/01 | |
| Mike Harvey | $125,000 | 12/17/00 | |
| David Honea | $125,000 | 08/18-19/99, 08/29/99 | (see below) |
| Paul Hougland | $125,000 | 05/09/00 | Phoned Eddie Timanus |
| Mike Hughes | $125,000 | 03/19/00 | |
| Leigh Jaunsen | $125,000 | 04/20-23/00 | |
| Fowler Jones, III | $125,000 | 12/13-14/00 | |
| Lauren Kelner | $125,000 | 11/23-24/99 | |
| John Kerr | $125,000 | 03/11/01 | |
| Steve Kummer | $125,000 | 03/05-07/00 | |
| John LaMantia | $125,000 | 11/11-12/99 | |
| Suzy Law | $125,000 | 03/16-27/01 | |
| Maureen Lawlor | $125,000 | 07/11-13/00 | |
| Jack Lechner | $125,000 | 02/06/00 | Famous movie screenwriter |
| Derek Leif | $125,000 | 02/28/00 | |
| Michael Lowenstein | $125,000 | 11/02-05/00 | |
| Bill MacDonald | $125,000 | 08/26-27/99 | Won $126,399 on "Jeopardy!" |
| Joe Mallon | $125,000 | 10/31-11/01/00 | |
| Americo Mariota | $125,000 | 10/04/01 | |
| Kristine Marklein | $125,000 | 12/06-07/00 | Phoned Eddie Timanus |
| Jody Matzer | $125,000 | 05/30-31/00 | |
| Paul McCallon | $125,000 | 08/10/00 | |
| Dave McCarthy | $125,000 | 02/07/01 | |
| Jason McClung | $125,000 | 06/13/00 | |
| Rob McDaniel | $125,000 | 09/03-05/00 | |
| Edison McIntyre | $125,000 | 02/02-03/00 | |
| Kevin McSwain | $125,000 | 12/10-12/00 | |
| Michael Mernin | $125,000 | 07/09/00 | |
| Al Metz | $125,000 | 11/18/99 | |
| Jennifer Morgan | $125,000 | 08/06-08/00 | (see below) |
| Joe Mulcahey | $125,000 | 10/08-10/00 | |
| David Murphy | $125,000 | 12/27/01 | |
| Zalman Nakhimovsky | $125,000 | 08/16/01 | |
| Dan Nevarez | $125,000 | 10/19/00 | |
| Arthur O'Leary | $125,000 | 02/16-18/01 | |
| Kevin O'Neill | $125,000 | 01/31-02/01/01 | |
| Jane Oviatt | $125,000 | 11/21-22/99 | |
| Jason Parker | $125,000 | 06/26/01 | |
| Paul Pearson | $125,000 | 03/09/01 | |
| Mark Peterson | $125,000 | 02/03/00 | |
| Omer Poirier | $125,000 | 07/06/00 | |
| Mark Prysant | $125,000 | 02/22-23/00 | |
| Tom Rainard | $125,000 | 08/06/00 | |
| Tim Reilly | $125,000 | 11/18/99 | |
| Paul Riecke | $125,000 | 09/17/00 | |
| Andres Rivera | $125,000 | 11/14/99 | |
| Alexis Rodriguez | $125,000 | 05/23/02 | Ladies Nights |
| Don Rohan | $125,000 | 01/29/00 | Super Bowl Edition |
| Michael Rosenthal | $125,000 | 08/27-28/99 | |
| Marcus Schick | $125,000 | 01/11-12/01 | |
| Bob Shick | $125,000 | 05/11/00 | |
| Michael Shveima | $125,000 | 11/22/00 | |
| Brian Sigrist | $125,000 | 04/30/00 | |
| Eric Simon | $125,000 | 02/04/01 | |
| Jay Snyder | $125,000 | 10/01/00 | |
| Jennifer Stoner | $125,000 | 06/14/01 | |
| Andrew Strange | $125,000 | 10/10/00 | |
| Travis Sumner | $125,000 | 11/11-12/01 | Armed Forces |
| Tom Syta | $125,000 | 01/18/01 | Brother of Jim Syta |
| Gayle Takasaki | $125,000 | 02/23/01 | |
| Helga Toriello | $125,000 | 02/16/01 | |
| Ron Trigueiro | $125,000 | 05/11-14/00 | Won $50,401 on "Jeopardy!" |
| Heather Urbanski | $125,000 | 06/27/02 | |
| Warunchai Vathanasin | $125,000 | 04/04-11/02 | |
| Bob Watts | $125,000 | 04/06-09/00 | |
| Tom Wheltle | $125,000 | 09/12-14/00 | |
| Jim White | $125,000 | 04/02/00 | |
| Jonathan Wilks | $125,000 | 02/20/00 | |
| Sam Wolfe | $125,000 | 04/13-15/01 | |
| Annamaria Zavala | $125,000 | 12/20/01 | |
| Charles Anderson | $64,000 | 01/29/00 | Super Bowl Edition |
| Lance Baker | $64,000 | 06/12/01 | |
| Jim Baldwin | $64,000 | 08/20/00 | |
| Judy Bartoletti | $64,000 | 07/06-09/00 | Phoned Steve Cornman |
| Bill Beattie | $64,000 | 10/10-11/00 | |
| Bill Berry | $64,000 | 03/01/00 | |
| Steve Best | $64,000 | 06/04-06/00 | |
| Scott Bickerstaff | $64,000 | 04/23-27/00 | |
| Ryan Biederman | $64,000 | 03/16/00 | |
| Richard Boleman | $64,000 | 04/26/01 | |
| John Booth | $64,000 | 02/18-21/01 | |
| Sidney Browning | $64,000 | 03/07-08/01 | |
| Dianne Buchek | $64,000 | 06/11/00 | |
| Becky Busby | $64,000 | 05/30/02 | Ladies Nights |
| Moira Casillas | $64,000 | 12/20-27/01 | |
| Jim Cleaves | $64,000 | 06/05-10/01 | |
| Tara Collins | $64,000 | 03/15/01 | |
| Douglas Collum | $64,000 | 08/26/01 | |
| Frank Cook | $64,000 | 09/27/01 | |
| Maria Costanzo | $64,000 | 04/13/01 | |
| Todd Creekmore | $64,000 | 06/15-18/00 | |
| Ellen Cutler | $64,000 | 06/21/01 | |
| Anne Davis | $64,000 | 04/16/00 | |
| Peter Diamond | $64,000 | 03/16/01 | |
| Bob DiGiusto | $64,000 | 04/06/00 | |
| John Dignam | $64,000 | 01/11/01 | |
| James Dinan | $64,000 | 04/05/01, 05/21/01 | Zero Winners Edition (missed Q5); Won $5,000 on "ESPN 2-Minute Drill" |
| Mike DiStefano | $64,000 | 10/25/01 | |
| Brian Duray | $64,000 | 09/14/00 | |
| Carolyn Dushane | $64,000 | 02/17-20/00 | |
| Marge Edmiston | $64,000 | 09/07/00 | |
| Joe Erwin | $64,000 | 11/26-28/00 | |
| Steve Fayne | $64,000 | 02/20-22/00, 05/21/01 | Zero Winners Edition (missed Q5) |
| Mike Feinberg | $64,000 | 11/12-13/99 | |
| Kevin Fleming | $64,000 | 10/03-04/00 | |
| Jason Francis | $64,000 | 11/23/99 | |
| Mark Frankfother | $64,000 | 04/19-20/01 | |
| Adam & Leslie Fried | $64,000 | 02/14/02 | Couples Edition II |
| Jon Futrell | $64,000 | 03/25/00, 05/20/01 | Oscar Edition; Zero Winners Edition (missed Q2) |
| Jim Gilligan | $64,000 | 02/08/00 | |
| Matthew Gray | $64,000 | 11/29-30/00 | |
| Rick Grimes | $64,000 | 11/13/99 | Jason Block's PAF |
| Jeff Grizer | $64,000 | 01/25-27/00 | |
| Rob Hallworth | $64,000 | 02/23-24/00 | |
| Jamie Hammond | $64,000 | 08/20-22/00 | |
| Angie Hamrick | $64,000 | 05/03/01 | |
| Curtis Hane | $64,000 | 12/13/00 | |
| Phyllis Harris | $64,000 | 11/08/01 | Won $400,000 on "Greed" |
| Brad Herzog | $64,000 | 04/04/00 | Famous author |
| Ken Hesser | $64,000 | 01/11/00 | |
| Katharine Hinkle | $64,000 | 02/07/02 | College Week II |
| Kathryn Humphreys | $64,000 | 05/30/00 | |
| David Ippolito | $64,000 | 11/29/00 | |
| Ian Ith | $64,000 | 11/05-08/00 | |
| Andy Jackson | $64,000 | 06/12/01 | Diane Reul's PAF |
| Andrew Jankowski | $64,000 | 04/11/02 | |
| Pat Jones | $64,000 | 03/13/01 | |
| Emily June | $64,000 | 08/30/01 | |
| Sally Keenan | $64,000 | 02/01/01 | |
| Doug Kufahl | $64,000 | 06/24-26/01 | |
| Susan Larose | $64,000 | 10/03/00 | |
| Jim Laverty | $64,000 | 11/11/01 | Armed Forces |
| Scott Leff | $64,000 | 03/28/00 | |
| Matt Lester | $64,000 | 06/06-20/02 | |
| Paula Littman | $64,000 | 10/25/01 | |
| Lisa Lord | $64,000 | 05/16-17/00 | |
| Rich Mahady | $64,000 | 10/17-18/00 | |
| Casey Mallough & Molly Robison | $64,000 | 05/15/01 | Couples Edition I |
| Steve Malnar | $64,000 | 11/12/01 | Armed Forces |
| Jill Maxwell | $64,000 | 12/13/01 | |
| Jeff Mazurak | $64,000 | 03/02-05/00 | |
| Eddy McIntyre | $64,000 | 09/27/01 | |
| Jung Mi Lee | $64,000 | 02/07/02 | College Week II |
| Tom Michael | $64,000 | 04/20/01 | |
| Troy Miller | $64,000 | 05/14-16/00 | |
| Jennifer Mullins | $64,000 | 11/15-16/99 | |
| David Patrick | $64,000 | 11/22/99 | |
| Beth Plummer | $64,000 | 11/10-11/99 | |
| Penny Poplin Gosetti | $64,000 | 02/21-22/01 | |
| Dave Potts | $64,000 | 04/11/00 | |
| Amy Proctor Mantyla | $64,000 | 06/05/01 | |
| Trevor Pyle | $64,000 | 07/12/01 | |
| Alex Rachmiel | $64,000 | 01/28/01 | |
| Steve Reid | $64,000 | 06/26-28/01 | |
| Tom Reneau | $64,000 | 04/11/00 | |
| Tim Rogers | $64,000 | 07/20/00 | |
| Drew Rosin | $64,000 | 01/25/00 | |
| Dan Rufer | $64,000 | 03/15-16/01 | |
| Kevin Rupe | $64,000 | 04/10/01 | |
| Justin & Lorraine Savino | $64,000 | 02/14/02 | Couples Edition II |
| Jessica Schreader | $64,000 | 04/29/01 | Won $2,000 on "Jeopardy!" |
| Jason Scott | $64,000 | 04/22-24/01 | |
| Charlotte Seymour | $64,000 | 11/08-09/00 | |
| Larry Shackley | $64,000 | 04/03/01 | |
| Lori Shiels | $64,000 | 02/01/00 | |
| Jeff Siehl | $64,000 | 11/08/99 | |
| Matt Silcox | $64,000 | 09/17-19/00 | |
| Tammy Smutny | $64,000 | 08/14-16/01 | |
| Dan Stewart | $64,000 | 02/02/01 | |
| Andrea Stout | $64,000 | 05/01-03/01 | |
| Stephanie Stradley | $64,000 | 05/23-30/02 | Ladies Nights; Houston Texans blogger for the "Houston Chronicle" |
| Kevin Swaluk | $64,000 | 08/08-10/00 | |
| Doug Szafran | $64,000 | 08/21-22/99 | |
| Randy Tomassi | $64,000 | 01/05-07/01 | |
| Anthony Torres & Anya Sanko | $64,000 | 05/15-16/01 | Couples Edition I |
| Jonathan Tsilimos | $64,000 | 03/28/02 | |
| Dane & Melissa Vaught | $64,000 | 02/28/02 | Couples Edition II |
| Barbara Von Pagel | $64,000 | 04/12/01 | |
| Rebecca Wallihan | $64,000 | 07/17/01 | |
| Shae Wilhite | $64,000 | 05/22-24/01 | |
| John Wilkes | $64,000 | 03/08/01 | |
| Jeff Wilkie | $64,000 | 01/10-11/00 | |
| Rob Wilson | $64,000 | 07/19/01 | Husband of Debbie Wilson |
| Joel Winkelsas | $64,000 | 11/08-09/99 | |
| Ben Wong | $64,000 | 12/19-20/00 | College Week I; Won $2,000 on "Jeopardy!" |
| Jason Wong | $64,000 | 01/19/01 | |
| Maegen Worley | $64,000 | 04/19/01 | |
| Scott Yackel | $64,000 | 10/01-03/00 | |
| Christopher Young | $64,000 | 08/23-26/01 |
Footnotes:
--Toutant's 01/31/01 appearance was cut short by incorrectly answering a flawed $16,000 question. The producers brought him back in May in an (originally) untelevised segment. Since he won the jackpot, the segment became a special half-hour episode in September.
--Shields' 01/14/00 appearance was cut short by incorrectly answering a flawed $16,000 question. The producers later brought him back in an untelevised segment.
--Honea's 11/19/99 appearance was cut short by incorrectly answering a flawed $64,000 question. The producers brought him back 10 days later.
--Morgan was a finalist on the 07/16/00 show, but a computer malfunction in her podium caused her to lose all of her Fastest Finger contests. The producers brought her back three weeks later.
