| 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. |
| Leakesville, MS | 5,443 | 45% | 6.3% |
| Creswell, OR | 5,445 | 47% | 2.1% |
| 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% |
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