| Event | Finish | Individual Highlights |
| Preseason Tournament of Champions | 2nd | Marina McDonald (Champion, Low Medal Class) Sara Hearn (Tenth-Place Competitor, High Medal Class) |
| Worcester State Show | 1st | Emy McLaughlin (Overall High Point Rider of the Day) Emy McLaughlin (High Point Limit Rider) Sara Hearn (Reserve High Point Rider) Katerina Alvarez (Reserve High Point Limit Rider) Indra Rapinchuk-Souccar (Reserve High Point Intermediate Rider) |
| Williams College | 2nd | Sarah Etzel (Reserve High Point Limit Rider) |
| Mount Holyoke Show | 1st | Libby Sams (Overall High Point Rider of the Day) Libby Sams (Intermediate High Point Rider) Sara Hearn (Reserve High Point Rider) Emy McLaughlin (Reserve Intermediate High Point Rider) Kristina Honour (Reserve High Point Limit Rider of the Day) |
| UMass Amherst Show | 1st | Sara Hearn (Overall High Point Rider of the Day) Johanna Sullivan (High Point Limit Rider) Emy McLaughlin (Reserve High Point Limit Rider of the Day) |
| Mount Holyoke Show | T-1st | Katerina Alvarez (High Point Rider of the Day) Katerina Alvarez (High Point Intermediate Title) Marina McDonald (Reserve High Point Limit Rider of the Day) |
| Holiday Tournament of Champions | 2nd | Sara Hearn (Third Place - Open Medal Fences) Sierra Dunn (Low Medal Finalist - Fences) |
| Winter Tournament of Champions | 4th | Sara Hearn (1st Place - High Medal) Franny Eremeeva (7th Place - High Medal) Indra Rapinchuk-Souccar (9th Place - High Medal) Sarah Etzel (8th Place - Low Medal) Marina McDonald (10th Place - Low Medal) |
| Smith College Show | 1st | Kristina Honour (Reserve Overall High Point Rider of the Day) |
| UMass Amherst Show | 1st | Kristina Honour (Reserve Limit High Point Rider of the Day) Sierra Dunn (Overall and Intermediate High Point Rider of the Day) |
| Mount Holyoke Show | 1st | Kristina Lester (Overall High Point Rider of the Day) Sarah Etzel (Reserve High Point Rider of the Day) Emy McLaughlin (Intermediate High Point Rider of the Day) Claire Williams (Reserve Limit High Point Rider of the Day) |
| Remainder of season was cancelled due to COVID-19 pandemic. | ||