| Index | Winston | Oregon | National |
| Average Test Scores | 29% | 46% | 48% |
| Student/Teacher ratio | 20:1 | 20:1 | 16:1 |
| Total public schools | 5 | 1,097 | 79,221 |
| Total private schools | 1 | 361 | 24,874 |
| Total post-secondary schools | n/a | 89 | 7,963 |
| Index | Winston | Oregon | National |
| Completed 8th grade | 83.0% | 86.3% | 84.3% |
| Completed high school | 82.3% | 85.4% | 83.0% |
| Completed some college | 52.4% | 66.1% | 59.4% |
| Completed associate degree | 21.6% | 39.9% | 38.5% |
| Completed bachelors | 9.2% | 31.4% | 30.3% |
| Completed masters | 2.9% | 11.9% | 11.5% |
| Completed professional degree | 1.3% | 3.6% | 3.3% |
| Completed doctorate | 0.7% | 1.5% | 1.3% |
There are a total of 5 public schools, 1 private schools and n/a post-secondary schools in Winston. Using the proficiency score averages, the average test scores for Winston, OR schools is 29%. The average student to teacher ratio is 20:1. In Winston, OR, an average of 83.0% of students have completed 8th grade and an average of 82.3% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Dillard, OR | 525 | 50% | 4.2% |
| Roseburg, OR | 23,237 | 42% | 12.2% |
| Myrtle Creek, OR | 3,447 | 37% | 22.1% |
| Canyonville, OR | 1,812 | 37% | 22.9% |
| Roseburg North, OR | 4,328 | 35% | 28.1% |
| Winston, OR | 5,444 | 29% | 40.4% |
| City | Population | Avg. Test Scores | National Avg. |
| Creswell, OR | 5,445 | 47% | 2.1% |
| Leakesville, MS | 5,443 | 45% | 6.3% |
| Rockwood, TN | 5,446 | 31% | 35.4% |
| Coraopolis, PA | 5,448 | 49% | 1.7% |
| Cottleville, MO | 5,439 | 69% | 43.1% |
| Winston, OR | 5,444 | 29% | 40.4% |
Here are the best places to live in Oregon
Check out the 10 safest cities in Oregon
These are the 10 cheapest cities in Oregon
Check out the 10 most dangerous cities in Oregon