| | PG | Traded (The Portland Trail Blazers traded G Jrue Holiday to the Boston Celtics.) To |
| | SG | Signed/Offer Sheet (The Portland Trail Blazers signed G Skylar Mays.) |
| | PG | Traded (The Boston Celtics traded G Malcolm Brogdon to the Portland Trail Blazers.) From |
| | C | Traded (The Boston Celtics traded C Robert Williams III to the Portland Trail Blazers.) From |
| | PF | Traded (The Phoenix Suns traded F Toumani Camara to the Portland Trail Blazers.) From |
| | PF | Traded (The Portland Trail Blazers traded F-G Nassir Little to the Phoenix Suns.) To |
| | SG | Traded (The Portland Trail Blazers traded G Keon Johnson to the Phoenix Suns.) To |
| | C | Traded (The Phoenix Suns traded C Deandre Ayton to the Portland Trail Blazers.) From |
| | PG | Traded (The Milwaukee Bucks traded G Jrue Holiday to the Portland Trail Blazers.) From |
| | PG | Traded (The Portland Trail Blazers traded G Damian Lillard to the Milwaukee Bucks.) To |
| | C | Traded (The Portland Trail Blazers traded C Jusuf Nurkic to the Phoenix Suns.) To |
| | C | Signed/Offer Sheet (The Portland Trail Blazers signed C Duop Reath.) |
| | PF | Signed/Offer Sheet (The Portland Trail Blazers signed F George Conditt IV.) |
| | C | Signed/Offer Sheet (The Portland Trail Blazers signed C Moses Brown. ) |
| | SG | Waived (The Portland Trail Blazers waived G Jeenathan Williams.) |
| | SG | Re-Signed (The Portland Trail Blazers re-signed G-F Matisse Thybulle.) |
| | C | Re-Signed (The Portland Trail Blazers re-signed F John Butler Jr.) |
| | C | Signed/Offer Sheet (The Portland Trail Blazers signed C Ibou Badji to a two-way contract. ) |
| | C | Declared Free Agency (C Chance Comanche declared free agency.) |
| | PF | Waived (The Portland Trailblazers waived F Trendon Watford.) |
| | PF | Signed/Offer Sheet (The Portland Trail Blazers signed F Jerami Grant.) |
| | SF | Declared Free Agency (F-G Justise Winslow declared free agency.) |
| | SG | Declared Free Agency (G-F Matisse Thybulle declared free agency.) |
| | C | Declared Free Agency (F John Butler Jr. declared free agency.) |
| | SF | Declared Free Agency (F-G Cam Reddish declared free agency.) |
| | C | Declared Free Agency (F-C Drew Eubanks declared free agency.) |
| | PF | Declared Free Agency (F Jerami Grant declared free agency.) |
| | SG | Declared Free Agency (G Skylar Mays declared free agency.) |
| | C | Declared Free Agency (C Ibou Badji declared free agency.) |
| | PG | Signed as Draft Pick (The Portland Trail Blazers drafted G Scoot Henderson.) |
| | SG | Waived (The Portland Trail Blazers waived G Shaquille Harrison.) |
| | SG | Waived (The Portland Trail Blazers waived G Skylar Mays.) |
| | C | Signed/Offer Sheet (The Portland Trail Blazers signed C Chance Comanche.) |
| | SG | Signed/Offer Sheet (The Portland Trail Blazers signed G Skylar Mays.) |
| | SF | Signed to 10-Day Contract (The Portland Trail Blazers signed F Justin Minaya to a 10-Day Contract.) |
| | SG | Signed/Offer Sheet (The Portland Trail Blazers signed G-F Jeenathan Williams.) |
| | PG | Waived (The Portland Trail Blazers waived G Ryan Arcidiacono.) |
| | SG | Signed to 2nd 10-Day Contract (The Portland Trailblazers signed G Shaquille Harrison to a 10-day contract.) |
| | SG | Signed to 10-Day Contract (The Portland Trailblazers signed G Skylar Mays to a 10-day contract.) |