| Index | Winston | Missouri | National |
| Average Test Scores | 43% | 44% | 48% |
| Student/Teacher ratio | n/a | 14:1 | 16:1 |
| Total public schools | n/a | 1,899 | 79,221 |
| Total private schools | n/a | 531 | 24,874 |
| Total post-secondary schools | n/a | 213 | 7,963 |
| Index | Winston | Missouri | National |
| Completed 8th grade | 68.9% | 86.0% | 84.3% |
| Completed high school | 66.7% | 84.2% | 83.0% |
| Completed some college | 28.2% | 57.7% | 59.4% |
| Completed associate degree | 6.8% | 35.2% | 38.5% |
| Completed bachelors | 3.4% | 27.6% | 30.3% |
| Completed masters | 1.7% | 10.4% | 11.5% |
| Completed professional degree | 1.1% | 2.8% | 3.3% |
| Completed doctorate | 0.0% | 1.2% | 1.3% |
There are a total of n/a public schools, n/a private schools and n/a post-secondary schools in Winston. Using the proficiency score averages, the average test scores for Winston, MO schools is 43%. The average student to teacher ratio is n/a. In Winston, MO, an average of 68.9% of students have completed 8th grade and an average of 66.7% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Cameron, MO | 8,941 | 51% | 6.9% |
| Osborn, MO | 402 | 50% | 4.2% |
| Hamilton, MO | 1,988 | 49% | 1.0% |
| Gallatin, MO | 1,674 | 45% | 6.9% |
| Maysville, MO | 1,142 | 45% | 7.3% |
| Winston, MO | 216 | 43% | 11.5% |
| City | Population | Avg. Test Scores | National Avg. |
| Willow Creek, MT | 216 | 45% | 6.3% |
| Port Murray, NJ | 216 | 47% | 2.1% |
| Cypress, IL | 216 | 18% | 63.5% |
| Albin, WY | 216 | 70% | 45.8% |
| San Jon, NM | 216 | 48% | 0.7% |
| Winston, MO | 216 | 43% | 11.5% |
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