Search Results
| Date | Team | Acquired | Relinquished | Notes |
| 1999-01-21 | Cavaliers | • Shawn Harlan | signed free agent to a non-guaranteed contract | |
| 1999-01-22 | Cavaliers | • Ryan Stack | signed second round pick to a non-guaranteed contract | |
| 1999-01-24 | Cavaliers | • Charlie Melvin | waived | |
| 1999-01-24 | Cavaliers | • Damon Bailey | waived | |
| 1999-01-24 | Cavaliers | • Rocky Walls | waived | |
| 1999-01-24 | Cavaliers | • Johnny Newman | signed free agent to a 2-year, $2.1M contract | |
| 1999-01-27 | Cavaliers | • Shawn Harlan | waived | |
| 1999-01-29 | Cavaliers | • Zydrunas Ilgauskas | re-signed to a 6-year $70.9M contract extension | |
| 1999-02-02 | Cavaliers | • Carlos Strong | waived | |
| 1999-02-02 | Cavaliers | • Otis Hill | waived | |
| 1999-02-04 | Cavaliers | • Roy Rogers | signed free agent | |
| 1999-02-17 | Cavaliers | • Litterial Green | waived | |
| 1999-02-17 | Cavaliers | • Roy Rogers | waived | |
| 1999-03-10 | Cavaliers | • Antonio Lang | waived | |
| 1999-03-10 | Cavaliers | • Mitchell Butler | waived | |
| 1999-03-10 | Cavaliers | • Earl Boykins | signed free agent to a 10-day contract | |
| 1999-03-11 | Cavaliers | • Andrew DeClercq • first round pick (Cavaliers option of 1999 (protected top 3), 2000, 2001) (1999 #8-Andre Miller) |
• Vitaly Potapenko | trade with Celtics |
| 1999-03-13 | Cavaliers | • Corie Blount | signed free agent | |
| 1999-03-19 | Cavaliers | • Earl Boykins | waived | |
| 1999-03-19 | Cavaliers | • Mitchell Butler | signed free agent for the remainder of the season | |
| 1999-03-23 | Cavaliers | • Earl Boykins | signed free agent to a second 10-day contract | |
| 1999-04-02 | Cavaliers | • Earl Boykins | re-signed for the remainder of the season | |
| 1999-06-01 | Cavaliers | • Mike Fratello | fired as head coach | |
| 1999-06-01 | Cavaliers | • Wayne Embry | resigned as GM | |
| 1999-06-01 | Cavaliers | • Jim Paxson (Jr.) | promoted to general manager |
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