| Index | Winona | Mississippi | National |
| Average Test Scores | 31% | 40% | 48% |
| Student/Teacher ratio | 15:1 | 16:1 | 16:1 |
| Total public schools | 3 | 893 | 79,221 |
| Total private schools | 1 | 206 | 24,874 |
| Total post-secondary schools | n/a | 68 | 7,963 |
| Index | Winona | Mississippi | National |
| Completed 8th grade | 63.6% | 78.6% | 84.3% |
| Completed high school | 60.1% | 76.7% | 83.0% |
| Completed some college | 36.4% | 52.5% | 59.4% |
| Completed associate degree | 22.9% | 29.8% | 38.5% |
| Completed bachelors | 19.7% | 21.0% | 30.3% |
| Completed masters | 7.9% | 7.9% | 11.5% |
| Completed professional degree | 1.1% | 2.2% | 3.3% |
| Completed doctorate | 0.0% | 0.9% | 1.3% |
There are a total of 3 public schools, 1 private schools and n/a post-secondary schools in Winona. Using the proficiency score averages, the average test scores for Winona, MS schools is 31%. The average student to teacher ratio is 15:1. In Winona, MS, an average of 63.6% of students have completed 8th grade and an average of 60.1% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| North Carrollton, MS | 365 | 26% | 46.9% |
| Winona, MS | 4,099 | 31% | 36.5% |
| City | Population | Avg. Test Scores | National Avg. |
| Burgaw, NC | 4,101 | 42% | 13.0% |
| Ho-Ho-Kus, NJ | 4,096 | 85% | 77.1% |
| Rogersville, MO | 4,096 | 44% | 7.8% |
| Lonsdale, MN | 4,102 | 67% | 39.6% |
| Sinking Spring, PA | 4,104 | 61% | 27.5% |
| Winona, MS | 4,099 | 31% | 36.5% |
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