September 15, 1999: Buffalo signs Chad Curtis, Donovan Osborne and Russ Springer; cuts Willie Greene, Tony Phillips, and Jason McDonald.
Septermber 11, 1999: San Francisco signs Carlos Guillen; cuts Derrick Gibson.
Seattle signs Ron Villone; cuts Bill Taylor.
Baton Rouge signs Bill Taylor; cuts Danny Patterson.
September 9, 1999: Cuyahoga signs Paul Sorrento; cuts Tom Candiotti.
September 8, 1999: Cleveland Rockers sign Jeffrey Hammonds; cut Scott Karl.
September 4, 1999: Cleveland Rockers trade Aramis Ramirez to San Francisco for Darrin Fletcher.
Red Arrow signs Denny Hocking and Jacob Cruz; cut Mark Lemke.
August 31, 1999 (all post-draft waivers and cutdown):
New York: Cut-Mark Wohlers
Pennsylvania: Signed-Ryan Demster, Jeremy Powell, David Ortiz, Mike MacFarlane, James Baldwin, Rafael Roque and Abraham Nunez; Cut-Greg Zaun, Domingo Cedeno, Jermaine Allensworth, Midre Cummings, Mike Morgan, Patterson, Jose Mesa
Red Arrow: Signed- Dave Magadan, C.J. Nitkowski, Matt Luke and Chad Bradford; Cut-Mike Cather, Brad Clontz, Matt Karchner, Willie McGee, Aaron Small, Dan Serafini, A.J. Sager, Willie Blair
Mt. Springs: Signed-Garret Stephenson, Bobby Chouinard and Bryce Florie; Cut-
Buffalo: Signed-Tim “Rock” Raines, Tony Phillips, Randy Winn, Gregg Jeffries, Kirt Manwaring, Lenny Webster, Esteban Yan, Esteban Loaiza, Ozzie Guillen, Willie Greene and Dennis Martinez; Cut-Geronimo Berroa, Jim Bullinger, Mathews, Jason Jacome, Mark Parent, Tyler Houston, Jacob Cruz, Russ Branyan, Jeffrey Hammonds, Chris Hoiles, Jimmy Haynes and Nerio Rodriguez
Cleveland Indians: Signed-Einar Diaz, Travis Miller, Al Reyes and Damon Croushore; Cut-Paul Assenmacher, Rich DeLucia, Eric Plunk, Lenny Webster, Kevin Sefcik and Keith Lockhart
Cleveland Rockers: Signed-Javier Vazquez, Aramis Ramirez, Fernando Seguinol; Cut-Donovan Osbourne, Jason Dickson, Esteban Loaiza, Jeff King, Eddie Guardado and Jose Vizcaino
Cuyahoga: Signed-Scott Aldred and Mike Fetters; Cut-Tim Bogar, Juan Samuel, Darren Hall and Scott Kaminiecki.
Bergman: Signed-A.J. Hinch, Greg Norton, Donnie Sadler and Jin Ho Cho; Cut-Sal Fasano, Reggie Jefferson, Joe Hudson and Rafael Bournigal.
Baton Rouge: Signed-Xavier Hernandez, Sean Runyan, Curtis Leskanic, Jeff Reboulet and Scott Service; Cut-Mike MacFarlane, Eduardo Perez, Mike Stanton, Frank Castillo and Bobby Witt
Florida: Signed-Dennis Springer, Vic Darensbourg, Jorge Fabregas and Brian Edmonson; Cut-Pat Borders, Turner Ward, Danny Darwin, Glendon Rusch and Marc Pisciotta
St. Pete: Signed- Randall Simon, Brook Fordyce, Mike Maddux, Paul Assenmacher and Charlie O’Brien; Cut-Benito Santiago, Lenny Harris, Pep Harris, Kent Mercker, Derrek Lee, Chris Stynes and Bob Tewksbury
Seattle: Signed-Matt Mieske, Alex Ochoa, Edgard Clemente, Ricky Ledee, Ricky Bones and Paul Abbott; Cut-Terry Adams, Paul Sorrento, Rich Amaral and Joey Cora.
San Francisco: Signed-Craig Wilson, Derrick Gibson, Daryle Ward; Cut-Rivera, Jim Abbott and Jose Cruz, Jr.
West L.A.: Signed-Javier Valentin, John Snyder, Jerry Hairston, Blake Stein, Carlton Loewer, Mike Judd, Todd Hollandsworth, and Kevin Sefcik; Cut-Paul Molitor, Dave Magadan, James Baldwin, Willie Greene, Bobby Estalella, and Jeff Juden
August 30, 1999: Baltimore Orioles officially move to Buffalo
August 24, 1999: Fresno trades Adrian Beltre to Cleveland Rockers for Troy Glaus.
August 23, 1999: Florida trades Jeff Conine to Red Arrow for Woody Williams.
August 21, 1999: BBL Draft
August 14, 1999: St. Pete Roses trade Magglio Ordonez, Mike Remlinger and their 2nd and 3rd Round draft choices to Cleveland Indians for Kevin Tapani, Kenny Lofton, Cliff Floyd, Kevin Millwood and Eric Young.
July 30, 1999: Pennsylvania Pikers trade Rich Loiselle and Garret Anderson to Fresno Outlaws for Bob Wickman and Fresno’s 3rd Round draft choice.
July 29, 1999: Seattle trades Alex Rodriguez, Tim Belcher and Paul Spoljaric to Cleveland Indians for Mike Hampton, Denny Neagle, Gary DiSarcina and Kerry Lightenberg.
July 27, 1999: Pennsylvania Pikers trade Andres Galarraga to Cleveland Indians for Jim Thome.
July 25, 1999: Pennsylvania Pikers trade Tony Womack to Seattle Mariners for Richard Hidalgo.
June 3, 1999: Cleveland Rockers trade Brian Giles and Mickey Morandini to the Pennsylvania Pikers for Francisco Cordova, Dan Plesac, and the Piker's #4 draft choice.
May 31, 1999: Bergman Colonels trade their 2nd and 5th round draft choices to the Cleveland Rockers for Doug Glanville.
May 25, 1999: San Francisco Waboritas trade Brad Ausmus and Shane Reynolds to Cuyahoga for Mike Piazza
May 23, 1999: West LA Fadeaway trade Tony Clark, Darren Oliver, Chris Gomez, and their 1st and 2nd round draft picks to Fresno for Pete Harnisch, Mark Grace, and John Franco.
May 23, 1999: West LA Fadeaway trades Brian Bohannon to Baton Rouge for Bobby Abreu.
May 23, 1999: Fresno Outlaws trade Rey Ordonez, Buddy Groom, and Jerry DiPoto to Cuyahoga for Raul Mondesi, Walt Weiss, and Luis Alicea.