Since the 2017–18 season, Portland and San Diego have met 20 times, and San Diego has the better of it at 12–8.
Most recently Portland won 87–74 on February 28, 2026.
Right now Portland is 0–0 and San Diego is 0–0, with San Diego at 223 days since a win against Portland's 222.
| Date | Site | Winner | Score |
|---|---|---|---|
| Sat, Feb 28 2026 | Portland home | Portland | 87–74 |
| Wed, Feb 11 2026 | San Diego home | San Diego | 71–58 |
| Sat, Mar 1 2025 | San Diego home | San Diego | 82–80 |
| Thu, Jan 23 2025 | Portland home | Portland | 92–82 |
| Thu, Feb 15 2024 | San Diego home | San Diego | 71–66 |
| Tue, Jan 23 2024 | Portland home | San Diego | 85–81 |
| Thu, Mar 2 2023 | Neutral site | Portland | 92–74 |
| Thu, Feb 2 2023 | San Diego home | Portland | 80–61 |
| Thu, Jan 19 2023 | Portland home | Portland | 88–83 |
| Fri, Mar 4 2022 | Neutral site | Portland | 73–55 |
| Thu, Feb 17 2022 | Portland home | Portland | 92–60 |
| Thu, Jan 13 2022 | San Diego home | San Diego | 68–63 |
| Sat, Jan 23 2021 | Portland home | San Diego | 78–70 |
| Sat, Feb 8 2020 | San Diego home | San Diego | 88–81 |
| Sat, Jan 18 2020 | Portland home | San Diego | 77–67 |
| Thu, Mar 7 2019 | Neutral site | San Diego | 67–47 |
| Thu, Feb 21 2019 | San Diego home | San Diego | 63–52 |
| Thu, Jan 17 2019 | Portland home | San Diego | 76–55 |
| Thu, Jan 18 2018 | San Diego home | Portland | 55–49 |
| Thu, Jan 4 2018 | Portland home | San Diego | 81–74 |
Full schedules and drought counters: Portland Pilots and San Diego Toreros.
Portland vs Denver, Portland vs Loyola Marymount, Portland vs Pacific, Portland vs Pepperdine, Portland vs Saint Mary's, Portland vs San Francisco, Portland vs Santa Clara, Portland vs Seattle U.
San Diego vs Denver, San Diego vs Loyola Marymount, San Diego vs Pacific, San Diego vs Pepperdine, San Diego vs Saint Mary's, San Diego vs San Francisco, San Diego vs Santa Clara, San Diego vs Seattle U.