| 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 | 536 | 50% | 4.2% |
| Roseburg, OR | 23,898 | 42% | 12.2% |
| Myrtle Creek, OR | 3,540 | 37% | 22.1% |
| Canyonville, OR | 1,876 | 37% | 22.9% |
| Roseburg North, OR | 4,473 | 35% | 28.1% |
| Winston, OR | 5,586 | 29% | 40.4% |
| City | Population | Avg. Test Scores | National Avg. |
| Stokesdale, NC | 5,586 | 60% | 24.0% |
| Preston, ID | 5,587 | 46% | 4.7% |
| Clarinda, IA | 5,584 | 61% | 26.0% |
| Cameron, TX | 5,589 | 40% | 17.4% |
| Sandersville, GA | 5,590 | 29% | 38.9% |
| Winston, OR | 5,586 | 29% | 40.4% |
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