| Sat, 01 Jan 2000 | Frank Jenkins / International Harvesters |
| Fri, 14 Jan 2000 | open mic / Atcher, Beck, and Kahl (open band) |
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Fri-Sat, 21-22 Jan 2000 |
Contra Swing Shift Fri in Lexington - Carol Kopp / Elise Melrood, Karen Jones, David Witherspoon, and Nathan Wilson Sat in Berea - Carol Kopp / The Berea Castoffs |
| Sat, 05 Feb 2000 | Mike Boerschig / Brittany Bay |
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Fri-Sat, 18-19 Feb 2000 |
Carnival Knowledge Lexington/Louisville weekend Fri in Lexington - Steve Bennett / Carnival Knowledge Sat in Louisville - Charley Harvey / Carnival Knowledge |
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Fri, 25 Feb 2000 |
Barbara Ramlow / The Biscuit Boys |
| Sat, 04 Mar 2000 | Tamara Loewenthal / The Monks |
| Fri, 10 Mar 2000 | Diane Silver / Atcher, Beck, and Kahl (open band) |
| Fri, 24 Mar 2000 | Keith Harding / Beyond the Pale |
| Sat, 08 Apr 2000 | Kath Tallichet / Bruce and Doug Greene |
| Fri, 14 Apr 2000 | Keith Cornett / Atcher, Beck, and Kahl (open band) |
| Fri, 28 Apr 2000 | Richard King / Al White and Elise Melrood |
| Sat, 06 May 2000 | Chris Bischoff / Ten Penny Bit |
| Fri, 12 May 2000 | open mic / Atcher, Beck, and Kahl (open band) |
| Fri, 26 May 2000 | Susan Petrick / Liam's Fancy |
| Fri-Sun, 09-11 Jun 2000 |
Dance Trance Lisa Greenleaf / Nightingale |
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Fri, 23 Jun 2000 |
Mike Finucane / Eve Podet, David Atcher, and Richard King |
| Sat, 01 Jul 2000 | Steve Bennett and Keith Harding / The Reel World String Band |
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Fri-Sat, 14-15 Jul 2000 |
Cailen Campbell Lexington/Louisville weekend Fri in Lexington - Cary Ravitz / Cailen Campbell and Jason Krekel Sat in Louisville - Joseph Pimentel / Cailen Campbell and Jason Krekel |
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Fri, 28 Jul 2000 |
Barbara Ramlow / Contrary Travelers |
| Sat, 05 Aug 2000 | Dwayne Johnson / Al White and Friends |
| Fri, 11 Aug 2000 | Steve Bennett / Beyond the Pale |
| Fri, 25 Aug 2000 | open mic / Atcher, Beck, and Kahl (open band) |
| Sat, 02 Sep 2000 | Chris Bischoff / The Corndrinkers |
| Fri, 08 Sep 2000 | Judy Goldsmith / Atcher, Beck, and Kahl (open band) |
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Fri-Sat, 22-23 Sep 2000 |
Hotpoint Lexington/Berea weekend Fri in Lexington - Caroline Fahrney / Hotpoint Sat in Berea - Charley Harvey / Hotpoint |
| Sat, 07 Oct 2000 | Mark Langner / The Briar Pickers (Jonathan Mays, Will Bacon, Jack Bunch) |
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Fri-Sat, 13-14 Oct 2000 |
Footloose Lexington/Cincinnati weekend Fri in Lexington - Keith Cornett / Footloose Sat in Cincinnati - Keith Cornett / Footloose |
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Fri, 27 Oct 2000 |
Barbara Ramlow / Atcher, Beck, and Kahl (open band) |
| Sat, 04 Nov 2000 | Darlene Underwood / The Trusty House Band |
| Fri, 10 Nov 2000 | Keith Harding / The Mink Run Consort |
| Fri, 17 Nov 2000 | Joseph Pimentel / The Groovemongers |
| Sat, 02 Dec 2000 | Kathy Anderson / The International Harvesters |
| Fri, 08 Dec 2000 | Keith Cornett / Atcher, Beck, and Kahl (open band) |