Roaring Twenty Trades: 1999

1998/99 Off-season/Pre-protection

• 12/17/98 Team 16 (Mike Vreeland) trades its 1st, 2nd, 3rd, and 5th expansion picks to Team 17 (Harlan Hendrick) for its 1st expansion pick.
• 12/19/98 Team 12 (Harris Jessop) trades its 2nd and 5th expansion picks to Team 13 (Theron Skyles) for its 1st and 12th expansion picks.
• 12/22/98 Team 16 (Mike Vreeland) trades its 4th expansion pick to Team 17 (Harlan Hendrick) for its 5th expansion pick and 12th regular draft pick.
• 12/26/98 Team 3 (Geoff Young) trades its 7th expansion pick and 31st regular draft pick to Team 19 (Thomas Love) for its 14th regular draft pick.
• 12/27/98 Team 3 (Geoff Young) trades its 8th expansion pick to Team 16 (Mike Vreeland) for its 18th regular draft pick.
• 12/27/98 Team 6 (Bob Holden/Paul Nielsen) trades its 7th and 10th expansion picks to Team 10 (Sam Arucan) for its 6th and 14th expansion picks.
• 12/29/98 Team 1 (Dan Young) trades 496 Matt Stairs and its 16th regular draft pick to Team 13 (Theron Skyles) for 73 Jaret Wright and its 10th regular draft pick.
• 12/29/98 Team 1 (Dan Young) trades 1372 Ben Petrick and 1441 Chad Hermansen to Team 16 (Mike Vreeland) for its 10th and 14th regular draft picks.
• 1/1/99 Team 11 (Michael Clark) trades 1533 Moises Alou and its 17th regular draft pick to Team 20 (Joel Bernstein) for 1594 Brian Jordan and its 15th regular draft pick.
• 1/3/99 Team 3 (Geoff Young) trades its 10th expansion pick to Team 19 (Thomas Love) for its 21st regular draft pick.
• 1/3/99 Team 12 (Harris Jessop) trades its 30th and 32nd regular draft picks to Team 16 (Mike Vreeland) for its 12th and 13th expansion picks.
• 1/5/99 Team 13 (Theron Skyles) trades its 24th regular draft pick to Team 16 (Mike Vreeland) for its 11th expansion pick.
• 1/6/99 Team 6 (Bob Holden/Paul Nielsen) trades its 25th and 28th regular draft picks to Team 14 (Tod Johnson) for 1235 Brad Penny and 1438 Ronnie Belliard.
• 1/7/99 Team 3 (Geoff Young) trades its 28th regular draft pick to Team 12 (Harris Jessop) for its 12th expansion pick.
• 1/8/99 Team 6 (Bob Holden/Paul Nielsen) trades its 29th regular draft pick to Team 17 (Harlan Hendrick) for its 12th expansion pick.
• 1/10/99 Team 14 (Tod Johnson) trades 322 Ramon Hernandez to Team 16 (Mike Vreeland) for its 28th regular draft pick.
• 1/12/99 Team 13 (Theron Skyles) trades its 23rd regular draft pick to Team 14 (Tod Johnson) for 1520 Brent Butler.
• 1/13/99 Team 7 (David McCormick) trades its 32nd and 33rd regular draft picks to Team 14 (Tod Johnson) for its 23rd and 25th regular draft picks.
• 1/18/99 Team 12 (Harris Jessop) trades its 32nd and 33rd regular draft picks to Team 13 (Theron Skyles) for its 26th and 31st regular draft picks
• 1/18/99 Team 14 (Tod Johnson) trades its 24th regular draft pick to Team 16 (Mike Vreeland) for Team 12's 32nd regular draft pick.

1998/99 Off-season/Post-protection

• 1/27/99 Team 6 (Bob Holden/Paul Nielsen) trades its 11th and 13th regular draft picks to Team 17 (Harlan Hendrick) for 1033 Dustin Hermanson.
• 1/31/99 Team 3 (Geoff Young) trades its 11th regular draft pick to Team 17 (Harlan Hendrick) for Team 6's 13th regular draft pick and Team 17's 16th regular draft pick.
• 2/1/99 Team 6 (Bob Holden/Paul Nielsen) trades its 12th and 19th regular draft picks to Team 19 (Thomas Love) for its 11th regular draft pick.
• 3/1/99 Team 1 (Dan Young) trades its 23rd regular draft pick to Team 14 (Tod Johnson) for its 26th and 31st regular draft picks.
• 3/20/99 Team 3 (Geoff Young) trades its 30th regular draft pick to Team 6 (Bob Holden/Paul Nielsen) for its 37th supplemental draft pick.

Regular Season

• 5/7/99 Team 6 (Bob Holden/Paul Nielsen) trades its 40th and 41st supplemental draft picks to Team 12 (Harris Jessop) for its 38th supplemental draft pick.
• 5/7/99 Team 11 (Michael Clark) trades its 38th supplemental draft pick to Team 14 (Tod Johnson) for its 40th and 43rd supplemental draft picks.
• 5/10/99 Team 6 (Bob Holden/Paul Nielsen) trades 1536 Doug Glanville to Team 18 (Lee Panas) for 1026 Mark Gardner and 1555 Mark Kotsay.
• 6/8/99 Team 1 (Dan Young) trades its 41st and 43rd supplemental draft picks to Team 12 (Harris Jessop) for its 44th supplemental draft picks and Team 6's 41st supplemental draft pick.
• 6/18/99 Team 5 (Jody Beaulac) trades Juan Encarnacion and Doug Mientkiewicz to Team 18 (Lee Panas) for Marvin Benard and Darin Erstad.
• 7/27/99 Team 12 (Harris Jessop) trades its 11th, 15th, 34th, and 35th regular draft picks to Team 19 (Thomas Love) for Chuck Knoblauch.
• 8/14/99 Team 3 (Geoff Young) trades its 15th regular draft pick to Team 20 (Joel Bernstein) for Bret Saberhagen.
• 8/14/99 Team 12 (Harris Jessop) trades its 13th and 20th regular draft picks to Team 20 (Joel Bernstein) for Jay Bell and Dave Mlicki.
• 8/15/99 Team 3 (Geoff Young) trades its 27th regular draft pick to Team 18 (Lee Panas) for Eddie Guardado.
• 8/15/99 Team 10 (Sam Arucan) trades its 17th regular draft pick to Team 18 (Lee Panas) for Chuck Finley.
• 8/15/99 Team 14 (Tod Johnson) trades its 21st and 25th regular draft picks to Team 18 (Lee Panas) for Kevin Tapani and Mike Trombley.
• 8/16/99 Team 1 (Dan Young) trades its 29th regular draft pick to Team 12 (Harris Jessop) for its 46th and 47th supplemental draft picks, and 31st regular draft pick.
• 8/16/99 Team 12 (Harris Jessop) trades its 36th supplemental draft pick to Team 16 (Charlie Wiles) for Richard Hidalgo.
• 8/17/99 Team 5 (Jody Beaulac) trades its 45th supplemental draft pick and 30th regular draft pick to Team 14 (Tod Johnson) for its 29th regular draft pick.
• 8/21/99 Team 3 (Geoff Young) trades its 22nd regular draft pick to Team 18 (Lee Panas) for Greg Swindell and its 27th regular draft pick.
• 8/28/99 Team 6 (Bob Holden/Paul Nielsen) trades Armando Reynoso, Jeff Shaw, and its 15th regular draft pick to Team 18 (Lee Panas) for Willie Blair and its 12th regular draft pick.
• 9/5/99 Team 1 (Dan Young) trades Chin Feng Chen to Team 19 (Thomas Love) for Brad Clontz, Doug Jones, and Matt Mantei.
• 9/5/99 Team 1 (Dan Young) trades George Lombard to Team 5 (Jody Beaulac) for Derek Lowe.
• 9/5/99 Team 3 (Geoff Young) trades its 26th regular draft pick to Team 16 (Charlie Wiles) for Dennys Reyes and its 31st regular draft pick.
• 9/5/99 Team 4 (Gary Johnson) trades its 35th regular draft pick and 36th supplemental draft pick to Team 16 (Charlie Wiles) for Ramon Hernandez.
• 9/5/99 Team 1 (Dan Young) trades Alex Gonzalez to Team 7 (David McCormick) for Graeme Lloyd and Paul Quantrill.