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- 1David Bagley vs. Brannon Denning vs. Kathy Donegan, Season Premiere, show #3151.September 7, 1998
- 2David Bagley vs. Barbara Bink vs. Tom Gould, show # 3152September 8, 1998
- 3David Bagley vs. Val Leith vs. John Allen Bankson, show # 3153.September 9, 1998
- 4David Bagley vs. Ed Gasparovic vs. Megan Clouser, show # 3154.September 10, 1998
- 5Megan Clouser vs. Marc Slutzky vs. Julie Schmitt, show # 3155.September 11, 1998
- 6Julie Schmitt vs. Faith Dawson vs. Paul Murray, show # 3156.September 14, 1998
- 7Paul Murray vs. Bill McLean vs. Anne Lanctot, show # 3157.September 15, 1998
- 8Anne Lanctot vs. Jenny Park vs. Lance Johnson, show # 3158.September 16, 1998
- 9Lance Johnson vs. Todd Schneider vs. Melissa Varvil, show # 3159.September 17, 1998
- 10Lance Johnson vs. Catherine Williamson vs. Fred Moten, show # 3160.September 18, 1998
- 11Lance Johnson vs. Emily Krucoff vs. John Brett, show # 3161.September 21, 1998
- 12Lance Johnson vs. Mary Flaherty vs. Dave Lasher, show # 3162.September 22, 1998
- 13Sharona Nelson vs. Hans Krimm vs. Colin Sheldon, show # 3163.September 23, 1998
- 14Hans Krimm vs. Barry Berlin vs. Faith Brown, show # 3164.September 24, 1998
- 15Hans Krimm vs. Barry Berlin vs. Marianne Vahey, show # 3165.September 25, 1998
- 16Barry Berlin vs. Jenny Winslow vs. Dan Mathews, show # 3166.September 28, 1998
- 17Barry Berlin vs. Carolyn White vs. Ben Holland, show # 3167.September 29, 1998
- 18Carolyn White vs. Lorraine Berry vs. Bob Phillips, show # 3168.September 30, 1998
- 19Carolyn White vs. Liz Holmlund vs. Tim Appling, show # 3169.October 1, 1998
- 20Carolyn White vs. Jordan Lees vs. Lawrence Brown, show # 3170.October 2, 1998
- 21Carolyn White vs. Reed Rankin vs. Heather Bell, show # 3171.October 5, 1998
- 22Heather Bell vs. Linda Zusman vs. Chuck Moul, show # 3172.October 6, 1998
- 23show # 3173.October 7, 1998
- 24Jonathan Silbert vs. Graham Powell vs. Melizza Zygmunt, show # 3174.October 8, 1998
- 25Melizza Zygmunt vs. Diane Pietrzak vs. Roger Clendening II, show # 3175.October 9, 1998
- 26Melizza Zygmunt vs. Margaret Boben vs. Alex Gershanik, show # 3176.October 12, 1998
- 27Melizza Zygmunt vs. Judy Squires vs. Miles Madorin, show 3177.October 13, 1998
- 28Melizza Zygmunt vs. Diane Green vs. David Glickman, show # 3178.October 14, 1998
- 29Diane Green vs. Walter Hanig vs. Elizabeth Bellas, show # 3179.October 15, 1998
- 30Diane Green vs. Tammy Talpas vs. Tim DeLamatre, show # 3180.October 16, 1998
- 31Tammy Talpas vs. Judie Cole vs. Dave Pedersen, show # 3181.October 19, 1998
- 32Tammy Talpas vs. Greg Sanders vs. Debra Winterton, show # 3182.October 20, 1998
- 33Greg Sanders vs. Eric Mercaldo vs. Ellen Yancey, show # 3183.October 21, 1998
- 34Ellen Yancey vs. Jennifer Young vs. Jamie Phillippe, show # 3184.October 22, 1998
- 35Jamie Phillippe vs. Ben Huston vs. Nancy Di Marino, show # 3185.October 23, 1998
- 36Jamie Phillippe vs. Juliet Wiley vs. Cres Heasley, show # 3186.October 26, 1998
- 37Juliet Wiley vs. Peter Iselin vs. Mia McIver, show # 3187.October 27, 1998
- 38Juliet Wiley vs. Gene Wurth vs. Pam Bybell, show # 3188.October 28, 1998
- 39Juliet Wiley vs. Rick Bunch vs. Liz Fasoldt, show # 3189.October 29, 1998
- 40Juliet Wiley vs. Michael Plank vs. Katie Clark, show # 3190.October 30, 1998
- 41Katie Clark vs. Sharon Doodian vs. Sinan Turnacioglu, show # 3191.November 2, 1998
- 42Sinan Turnacioglu vs. Jessica Ginsburg vs. Allen Upchurch, show # 3192.November 3, 1998
- 43Sinan Turnacioglu vs. Patty Leginus vs. Mark Sheehan, show # 3193.November 4, 1998
- 44Mark Sheehan vs. Tom Schellhammer vs. Debbie Thomas, show # 3194.November 5, 1998
- 451998 Celebrity Jeopardy! Legends in Sports Night. Show # 3195.November 6, 1998
- 461998 Boston Week game 1, show # 3196.November 9, 1998
- 471998 Boston Week game 2, show # 3197.November 10, 1998
- 481998 Boston Week game 3, show # 3198.November 11, 1998
- 491998 Boston Week game 4, show # 3199.November 12, 1998
- 501998 Boston Week game 5, show # 3200.November 13, 1998
- 511998 Teen Reunion Tournament preliminary game 1, show # 3201.November 16, 1998
- 521998 Teen Reunion Tournament preliminary game 2, show # 3202.November 17, 1998
- 531998 Teen Reunion Tournament preliminary game 3, show # 3203.November 18, 1998
- 541998 Teen Reunion Tournament preliminary game 4, show # 3204.November 19, 1998
- 551998 Teen Reunion Tournament final, show # 3205.November 20, 1998
- 56Harry Silverstein vs. Adriana Bate vs. Chris Sedlack, show # 3206.November 23, 1998
- 57Adriana Bate vs. Anne Robinson vs. Ross Lambersky, show # 3207.November 24, 1998
- 58Adriana Bate vs. Randy Juip vs. Coral Sullivan, show # 3208.November 25, 1998
- 59Adriana Bate vs. Deborah Danzis vs. Kemp Chester, show # 3209.November 26, 1998
- 60Deborah Danzis vs. Peter Warn vs. Julie Spencer, show # 3210.November 27, 1998
- 61Deborah Danzis vs. Dana Ezell vs. Andrew Maly, show # 3211.November 30, 1998
- 62Andrew Maly vs. Doug Higbee vs. Danielle Cast, show # 3212.December 1, 1998
- 63Andrew Maly vs. Alan Bone vs. Rebecca Reis, show # 3213.December 2, 1998
- 64Andrew Maly vs. Marc Danziger vs. Jayne Stallons, show # 3214.December 3, 1998
- 65Andrew Maly vs. Diane Wakefield vs. Brendan McTaggart, show # 3215.December 4, 1998
- 66Giselle Foss vs. Chris Seybolt vs. Mike Adams, show # 3216.December 7, 1998
- 67Giselle Foss vs. Megan Wood vs. John Zorn, show # 3217.December 8, 1998
- 68John Zorn vs. Georgia Routsis Savas vs. Gary Tish, show # 3218.December 9, 1998
- 69Gary Tish vs. Linda Bird vs. Budd Bailey, show # 3219.December 10, 1998
- 70Linda Bird vs. Bruce Monroe vs. Lucia Flevares, show # 3220.December 11, 1998
- 71Linda Bird vs. Patrick McElroy vs. Kristi Yacich, show # 3221.December 14, 1998
- 72Kristi Yacich vs. James Arey vs. Kathy Lester, show # 3222.December 15, 1998
- 73James Arey vs. Kristan Strietzel-Duga vs. Matt Bozulich, show # 3223.December 16, 1998
- 74James Arey vs. Joe Weber vs. Helen Harnett, show # 3224.December 17, 1998
- 75James Arey vs. Gina Diamante vs. Alan Cates, show # 3225.December 18, 1998
- 76James Arey vs. Erik Andersen vs. Martha Thomas, show # 3226.December 21, 1998
- 77Susan desJardins vs. Roger Goodman vs. Debra Keil, show # 3227.December 22, 1998
- 78Debra Keil vs. Gail Fouts Bernstein vs. John Hurst, show # 3228.December 23, 1998
- 79John Hurst vs. Devon Thomas vs. Dave Argentar, show # 3229.December 24, 1998
- 80Dave Argentar vs. Scott Speer vs. Will Thompson, show # 3230.December 25, 1998
- 81Will Thompson vs. Ron Mahla vs. Linda St. Clair-James, show # 3231.December 28, 1998
- 82Will Thompson vs. Colleen McSwiggin vs. Daniel Banando, show # 3232.December 29, 1998
- 83Colleen McSwiggin vs. Ardys Eserhut vs. Pete Fistanic, show # 3233.December 30, 1998
- 84Pete Fistanic vs. Felicia Vondrak vs. Brian Gillespie, show # 3234.December 31, 1998
- 85Show # 3235.January 1, 1999
- 86Brian Gillespie vs. Robb Borland vs. Peggy Sheehan, show # 3236.January 4, 1999
- 87Peggy Sheehan vs. Michael Cryer vs. April Hahn, show # 3237.January 5, 1999
- 88April Hahn vs. Dennis Thibodeaux vs. Lynn Crowel, show # 3238.January 6, 1999
- 89Dennis Thibodeaux vs. David Becker vs. Jill Rupert-Bennett, show # 3239.January 7, 1999
- 90David Becker vs. Wendy Salisbury vs. Kraig Norris, show # 3240.January 8, 1999
- 91David Becker vs. Leena Alam vs. Jeremy King, show # 3241.January 11, 1999
- 92Jeremy King vs. Laura Rhodes vs. Darren Davis, show # 3242.January 12, 1999
- 93Laura Rhodes vs. Pete Heinricher vs. Stacy Lammers, show # 3243.January 13, 1999
- 94Stacy Lammers vs. Mason Cole vs. Kristine Bachand, show # 3244.January 14, 1999
- 95Kristine Bachand vs. Kip Thompson vs. Jennifer Hawthorne, show # 3245.January 15, 1999
- 96Jennifer Hawthorne vs. Rich Hendricks vs. Michael Angel, show # 3246.January 18, 1999
- 97Rich Hendricks vs. Meaghan Parker vs. Prabal Chakrabarti, show # 3247.January 19, 1999
- 98Rich Hendricks vs. Will Salvini vs. Debra Bricker, show # 3248.January 20, 1999
- 99Debra Bricker vs. Mark Whittinghill vs. Laura McShane, show # 3249.January 21, 1999
- 100Mark Whittinghill vs. Earl Smith vs. Amy Rosenfeld, show # 3250.January 22, 1999
- 101Mark Whittinghill vs. Zach Biggs vs. Happy Aston, show # 3251.January 25, 1999
- 102Zach Biggs vs. Tonya Duus vs. Alex Huemer, show # 3252.January 26, 1999
- 103Alex Huemer vs. Lisa McAdam vs. Matt Sullivan, show # 3253.January 27, 1999
- 104Lisa McAdam vs. Karl Wallig vs. Patti Compton, show # 3254.January 28, 1999
- 105Karl Wallig vs. Paul Reisser vs. Caroline Walsh, show # 3255.January 29, 1999
- 106Paul Reisser vs. David Tate vs. Jenn Reilly, show # 3256.February 1, 1999
- 107David Tate vs. Cheryl Weiss vs. Matt Smith, show # 3257.February 2, 1999
- 108David Tate vs. Pat Martin vs. Josh Flosi, show # 3258.February 3, 1999
- 109Josh Flosi vs. Nathan Childs vs. Yen Bawagan, show # 3259.February 4, 1999
- 1101999 Celebrity Jeopardy! Leading Men Night, show # 3260.February 5, 1999
- 1111999 Tournament of Champions quarterfinal game 1, show # 3261.February 8, 1999
- 1121999 Tournament of Champions quarterfinal game 2, show #3262.February 9, 1999
- 1131999 Tournament of Champions quarterfinal game 3, show # 3263.February 10, 1999
- 1141999 Tournament of Champions quarterfinal game 4, show # 3264.February 11, 1999
- 1151999 Tournament of Champions quarterfinal game 5, show # 3265.February 12, 1999
- 1161999 Tournament of Champions semifinal game 1, show # 3266.February 15, 1999
- 1171999 Tournament of Champions semifinal game 2, show # 3267.February 16, 1999
- 1181999 Tournament of Champions semifinal game 3, show # 3268.February 17, 1999
- 1191999 Tournament of Champions final game 1, show # 3269.February 18, 1999
- 1201999 Tournament of Champions final game 2, show # 3270.February 19, 1999
- 1211999-A Teen Tournament quarterfinal game 1, show # 3271.February 22, 1999
- 1221999-A Teen Tournament quarterfinal game 2, show # 3272.February 23, 1999
- 1231999-A Teen Tournament quarterfinal game 3, show # 3273.February 24, 1999
- 1241999-A Teen Tournament quarterfinal game 4, show # 3274.February 25, 1999
- 1251999-A Teen Tournament quarterfinal game 5, show # 3275.February 26, 1999
- 1261999-A Teen Tournament semifinal game 1, show # 3276.March 1, 1999
- 1271999-A Teen Tournament semifinal game 2, show # 3277.March 2, 1999
- 1281999-A Teen Tournament semifinal game 3, show # 3278.March 3, 1999
- 1291999-A Teen Tournament final game 1, show # 3279.March 4, 1999
- 1301999-A Teen Tournament final game 2, show # 3280.March 5, 1999
- 131Nathan Childs vs. Laura Bowen vs. Dave Hampton, show # 3281.March 8, 1999
- 132Dave Hampton vs. Catherine Arnold vs. Randy Boudreaux, show # 3282.March 9, 1999
- 133Dave Hampton vs. Ellen Kellogg vs. Greg Sabin, show # 3283.March 10, 1999
- 134Ellen Kellogg vs. Kathleen Kinney vs. Steve Latourette, show # 3284.March 11, 1999
- 135Steve Latourette vs. Erin Weller vs. Dana Watrud, show # 3285.March 12, 1999
- 136Erin Weller vs. Robin McCreery vs. Michael Skeldon, show # 3286.March 15, 1999
- 137Robin McCreery vs. Betsy Mills vs. Lee Diveley, show # 3287.March 16, 1999
- 138Betsy Mills vs. Barry Hren vs. Rachel Stohl, show # 3288.March 17, 1999
- 139Barry Hren vs. Jeff Grimes vs. Cameron Soulis, show # 3289.March 18, 1999
- 140Jeff Grimes vs. Scott Tarapczynski vs. Linda Ferrazzara, show # 3290.March 19, 1999
- 1411999 Celebrity Jeopardy! Sports Anchors Night, show # 3291.March 22, 1999
- 142Jeff Grimes vs. Eric Brown vs. Robin LeMaster, show # 3292.March 23, 1999
- 143Robin LeMaster vs. Brad Nail vs. Susanne Sutton, show # 3293.March 24, 1999
- 144Brad Nail vs. Ajuan Mance vs. Brian Keenan, show # 3294.March 25, 1999
- 145Ajuan Mance vs. Dane Bevan vs. Beth Slattery, show # 3295.March 26, 1999
- 1461999 Celebrity Jeopardy! Sitcom Stars Night, show # 3296.March 29, 1999
- 147Ajuan Mance vs. Mihee Kim vs. Paul Rubenstein, show # 3297.March 30, 1999
- 148Ajuan Mance vs. Amy McEntee vs. Mike Lenahan, show # 3298.March 31, 1999
- 149Mike Lenahan vs. John Oleske vs. Michelle Roufa, show # 3299.April 1, 1999
- 150John Oleske vs. Karen Baptiste vs. Dan Inloes, show # 3300.April 2, 1999
- 1511999 Celebrity Jeopardy! TV Personalities Night, show # 3301April 5, 1999
- 152Dan Inloes vs. Kevin Knight vs. Mary Katz, show # 3302.April 6, 1999
- 153Mary Katz vs. Nancy Ellis vs. Chris Hartwell, show # 3303.April 7, 1999
- 154Mary Katz vs. Lynn McAleece vs. Bill Jacobs, show # 3304.April 8, 1999
- 155Bill Jacobs vs. Jimmy MacStravic vs. Elisabeth Zeller, show # 3305.April 9, 1999
- 1561999 Celebrity Jeopardy! Correspondents Night, show # 3306.April 12, 1999
- 157Bill Jacobs vs. Cheri Campbell vs. Victor Fanucci, show # 3307.April 13, 1999
- 158Bill Jacobs vs. Steve Bennett vs. Helen Petroff, show # 3308.April 14, 1999
- 159Helen Petroff vs. Beth Looney vs. Ed Clarke, show # 3309.April 15, 1999
- 160Helen Petroff vs. Richard Hill vs. Robin Travers, show # 3310.April 16, 1999
- 161Helen Petroff vs. Tim Buntel vs. Karen Rosenberg, show # 3311.April 19, 1999
- 162Helen Petroff vs. Christina Held-Hulsing vs. Eric Hemer, show # 3312.April 20, 1999
- 163Maria Valgenti vs. Edgar Smith, Jr. vs. Susan Hawks Wheeler, show # 3313.April 21, 1999
- 164Edgar Smith, Jr. vs. Louise Cornish vs. Tony Mangaser, show # 3314.April 22, 1999
- 165Edgar Smith, Jr. vs. Roberta Berg vs. Lindsay Peet, show # 3315.April 23, 1999
- 166Lindsay Peet vs. Scott Lewis vs. Shannon Poole, show # 3316.April 26, 1999
- 167Lindsay Peet vs. Mary Rider vs. Justin Scupine, show # 3317.April 27, 1999
- 168Lindsay Peet vs. Christian De Jong vs. Michael Rooney, show # 3318.April 28, 1999
- 169Michael Rooney vs. Dave Grove vs. Pamela Friedl, show # 3319.April 29, 1999
- 170Michael Rooney vs. Brien Wholey vs. Cindy Jacques, show # 3320.April 30, 1999
- 1711999 College Championship quarterfinal game 1, show # 3321.May 3, 1999
- 1721999 College Championship quarterfinal game 2, show # 3322.May 4, 1999
- 1731999 College Championship quarterfinal game 3, show # 3323.May 5, 1999
- 1741999 College Championship quarterfinal game 4, show # 3324.May 6, 1999
- 1751999 College Championship quarterfinal game 5, show # 3325.May 7, 1999
- 1761999 College Championship semifinal game 1, show # 3326.May 10, 1999
- 1771999 College Championship semifinal game 2, show # 3327.May 11, 1999
- 1781999 College Championship semifinal game 3, show # 3328.May 12, 1999
- 1791999 College Championship final game 1, show # 3329.May 13, 1999
- 1801999 College Championship final game 2, show # 3330.May 14, 1999
- 1811999-A Celebrity Jeopardy! game 1, show # 3331.May 17, 1999
- 1821999-A Celebrity Jeopardy! game 2, show # 3332.May 18, 1999
- 1831999-A Celebrity Jeopardy! game 3, show # 3333.May 19, 1999
- 1841999-A Celebrity Jeopardy! game 4, show # 3334.May 20, 1999
- 1851999-A Celebrity Jeopardy! game 5, show # 3335.May 21, 1999
- 186Michael Rooney vs. Abby Knight vs. Don Kaufman, show # 3336.May 24, 1999
- 187Michael Rooney vs. Andy Miller vs. Elena McFann, show # 3337.May 25, 1999
- 188Eileen Tremblay vs. Pat Smith vs. Elton Bowen, show # 3338.May 26, 1999
- 189Pat Smith vs. Alan Walters vs. Amy Iman, show # 3339.May 27, 1999
- 190Alan Walters vs. Melissa Koester vs. Ji Hee Seuk, show # 3340.May 28, 1999
- 191Melissa Koester vs. Frank Stokes vs. Jan Franck, show # 3341.May 31, 1999
- 192Frank Stokes vs. Susan Tull vs. Chris Culver, show # 3342.June 1, 1999
- 193Frank Stokes vs. Dave Martin vs. Seale Pylate, show # 3343.June 2, 1999
- 194Dave Martin vs. Marina Rimer vs. Preston Spickler, show # 3344.June 3, 1999
- 195Preston Spickler vs. Heather Rhodes vs. Kathy Grogman, show # 3345.June 4, 1999
- 196Kathy Grogman vs. Kit Salisbury vs. Paul Salcido, show # 3346.June 7, 1999
- 197Kit Salisbury vs. Sherry Rhodes vs. Will Austin, show # 3347.June 8, 1999
- 198Sherry Rhodes vs. Ryan Thiel vs. Kama Siegel, show # 3348.June 9, 1999
- 199Ryan Thiel vs. Jack Winters vs. Warren Barber Kertland, show # 3349.June 10, 1999
- 200Ryan Thiel vs. Michelle Arthington vs. Jerry Dynes, show # 3350.June 11, 1999
- 201Ryan Thiel vs. Chuck Lee vs. Sarah Gold, show # 3351.June 14, 1999
- 202Sarah Gold vs. Shannan Cvitanovic vs. Mike Scott, show # 3352.June 15, 1999
- 203Mike Scott vs. Wendi Harrell vs. Tim Lynch, show # 3353.June 16, 1999
- 204Mike Scott vs. Joe Padavic vs. Tammy King, show # 3354.June 17, 1999
- 205Joe Padavic vs. Kitty Estopinal vs. Adil Karim, show # 3355.June 18, 1999
- 206Joe Padavic vs. Sarah Simson vs. Terry Currin, show # 3356.June 21, 1999
- 207Terry Currin vs. Linda Poggensee vs. John Quaintance, show # 3357.June 22, 1999
- 208Terry Currin vs. Patrick Preston vs. Laurie Utterback, show # 3358.June 23, 1999
- 209Terry Currin vs. Kevin Fielder vs. Karin Travers, show # 3359.June 24, 1999
- 210Terry Currin vs. Norman Rogers vs. Dallas Dickinson, show # 3360.June 25, 1999
- 211Armed Forces Week game 1, show # 3361.June 28, 1999
- 212Armed Forces Week game 2, show # 3362.June 29, 1999
- 213Armed Forces Week game 3, show # 3363.June 30, 1999
- 214Armed Forces Week game 4, show # 3364.July 1, 1999
- 215Armed Forces Week game 5, show # 3365.July 2, 1999
- 216Sean McGinty vs. Corey Leahy vs. Jim Hammond, show # 3366.July 5, 1999
- 217Corey Leahy vs. Chris Sullivan vs. Clay Brown, show # 3367.July 6, 1999
- 218Corey Leahy vs. Paul Risner vs. Shelby Hammer, show # 3368.July 7, 1999
- 219Paul Risner vs. Suzy Fletcher vs. Terry Anderson, show # 3369.July 8, 1999
- 220Terry Anderson vs. Laura Miller vs. Doug Bennett, show # 3370.July 9, 1999
- 221Laura Miller vs. Brad Golstein vs. Jim Austgen, show # 3371.July 12, 1999
- 222Laura Miller vs. Franklin Leonard vs. Karen Skochinski, show # 3372.July 13, 1999
- 223Karen Skochinski vs. Katie Portnoy vs. Tom Crawford, show # 3373.July 14, 1999
- 224Tom Crawford vs. Vic Chandhok vs. Linda Lahnan, show # 3374.July 15, 1999
- 225Vic Chandhok vs. Mike Choyke vs. Ellen Lamb, show # 3375.July 16, 1999
- 226Vic Chandhok vs. Shane Richman vs. Mary Campbell, show # 3376.July 19, 1999
- 227Shane Richman vs. Martha Raphelson vs. Paul Graff, show # 3377.July 20, 1999
- 228Martha Raphelson vs. Diana Bush vs. Ed Case, show # 3378.July 21, 1999
- 229Martha Raphelson vs. Jackie Wollner vs. Jason Scupine, show # 3379.July 22, 1999
- 230Jackie Wollner vs. Geoff Morley vs. Peter Senkbeil, Season Finale, show #3380.July 23, 1999