| Index | Wineglass | Montana | National |
| Average Test Scores | n/a | 45% | 48% |
| Student/Teacher ratio | n/a | 14:1 | 16:1 |
| Total public schools | n/a | 408 | 79,221 |
| Total private schools | n/a | 77 | 24,874 |
| Total post-secondary schools | n/a | 32 | 7,963 |
| Index | Wineglass | Montana | National |
| Completed 8th grade | 90.2% | 89.4% | 84.3% |
| Completed high school | 90.2% | 88.2% | 83.0% |
| Completed some college | 73.7% | 63.1% | 59.4% |
| Completed associate degree | 52.7% | 38.6% | 38.5% |
| Completed bachelors | 47.3% | 29.9% | 30.3% |
| Completed masters | 12.2% | 9.8% | 11.5% |
| Completed professional degree | 12.2% | 3.0% | 3.3% |
| Completed doctorate | 12.2% | 1.2% | 1.3% |
There are a total of n/a public schools, n/a private schools and n/a post-secondary schools in Wineglass. Using the proficiency score averages, the average test scores for Wineglass, MT schools is n/a. The average student to teacher ratio is n/a. In Wineglass, MT, an average of 90.2% of students have completed 8th grade and an average of 90.2% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Livingston, MT | 7,696 | 47% | 1.7% |
| Wineglass, MT | 237 | n/a |
| City | Population | Avg. Test Scores | National Avg. |
| West Harrison, IN | 237 | 61% | 27.1% |
| Bluejacket, OK | 237 | 25% | 47.9% |
| Teller, AK | 237 | 10% | 79.2% |
| Fort Yates, ND | 237 | 10% | 80.2% |
| Hazelton, ND | 238 | 50% | 4.2% |
| Wineglass, MT | 237 | n/a |
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