| Index | Winona | Missouri | National |
| Average Test Scores | 54% | 44% | 48% |
| Student/Teacher ratio | 14:1 | 14:1 | 16:1 |
| Total public schools | 2 | 1,899 | 79,221 |
| Total private schools | n/a | 531 | 24,874 |
| Total post-secondary schools | n/a | 213 | 7,963 |
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| Index | Winona | Missouri | National |
| Completed 8th grade | 64.1% | 86.0% | 84.3% |
| Completed high school | 59.0% | 84.2% | 83.0% |
| Completed some college | 31.8% | 57.7% | 59.4% |
| Completed associate degree | 7.5% | 35.2% | 38.5% |
| Completed bachelors | 5.2% | 27.6% | 30.3% |
| Completed masters | 1.4% | 10.4% | 11.5% |
| Completed professional degree | 0.0% | 2.8% | 3.3% |
| Completed doctorate | 0.0% | 1.2% | 1.3% |
There are a total of 2 public schools, n/a private schools and n/a post-secondary schools in Winona. Using the proficiency score averages, the average test scores for Winona, MO schools is 54%. The average student to teacher ratio is 14:1. In Winona, MO, an average of 64.1% of students have completed 8th grade and an average of 59.0% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Eminence, MO | 625 | 46% | 4.7% |
| Birch Tree, MO | 629 | 45% | 7.3% |
| Winona, MO | 1,094 | 54% | 12.5% |
| City | Population | Avg. Test Scores | National Avg. |
| Monticello, WI | 1,094 | 37% | 22.6% |
| Pala, CA | 1,094 | 13% | 74.0% |
| Hector, MN | 1,093 | 50% | 3.1% |
| Gales Ferry, CT | 1,093 | 52% | 7.3% |
| Grand Meadow, MN | 1,095 | 53% | 10.4% |
| Winona, MO | 1,094 | 54% | 12.5% |
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