Search Results
| Date | Team | Acquired | Relinquished | Notes |
| 1999-07-16 | Bulls | • Fred Winter / Tex Winter | resigned as assistant coach | |
| 1999-07-26 | Bulls | • Elton Brand | signed first round pick to a 3-year, $8.9M contract with a fourth year, $3.9M team option | |
| 1999-08-03 | Bulls | • Charles Jones (Rahmel) | waived | |
| 1999-08-10 | Bulls | • Bill Berry | hired as assistant coach | |
| 1999-08-12 | Bulls | • Hersey Hawkins • James Cotton |
• Brent Barry | trade with Sonics |
| 1999-08-24 | Bulls | • Michael Ruffin | signed second round pick | |
| 1999-08-25 | Bulls | • Brett Robisch | signed free agent | |
| 1999-08-25 | Bulls | • Cory Carr | re-signed free agent | |
| 1999-08-25 | Bulls | • Lari Ketner | signed second round pick | |
| 1999-08-25 | Bulls | • Will Perdue | signed free agent to a reported 2-year $7M contract (second year is a team option) | |
| 1999-08-27 | Bulls | • Phil Johnson | hired as assistant coach | |
| 1999-08-30 | Bulls | • B.J. Armstrong | signed free agent to a 1-year minimum contract | |
| 1999-09-14 | Bulls | • Fred Hoiberg | signed free agent to a 1-year $800K contract | |
| 1999-09-16 | Bulls | • Ron Harper (Sr.) | renounced rights | |
| 1999-09-16 | Bulls | • Dickey Simpkins | re-signed free agent to a 1-year $2.3M contract | |
| 1999-09-22 | Bulls | • Keith Booth | waived | |
| 1999-09-27 | Bulls | • Don Haskins | hired as consultant | |
| 1999-09-29 | Bulls | • Chris Anstey | • 2000 second round pick (#31-Dan Langhi) | trade with Mavericks |
| 1999-10-04 | Bulls | • Doug Swenson | signed free agent | |
| 1999-10-04 | Bulls | • Maceo Baston | signed 1998 second round pick (signed free agent per Stats) | |
| 1999-10-19 | Bulls | • James Cotton | waived | |
| 1999-10-20 | Bulls | • Brett Robisch | waived | |
| 1999-10-20 | Bulls | • Maceo Baston | waived | |
| 1999-10-27 | Bulls | • Cory Carr | waived | |
| 1999-10-28 | Bulls | • Doug Swenson | waived |