| Date | Day | Event | Time | Location | Dress Code |
|---|---|---|---|---|---|
| May 1 | Tue | Tennis vs. Rutgers Prep (Home) | 3:45pm | Stuart Country Day School | |
| May 2 | Wed | Admission Open House | 9am | Manor House | |
| May 3 | Thu | Parents/Faculty Open Basketball Night | 6:30-8:30pm | Athletic & Convocation Center | |
| May 4 | Fri | First Friday Gathering | 9am First Friday Day of Recollection led by Father Patrick Connor, SVD | Princeton Academy Manor House | |
| May 4 | Fri | Cinco de Mayo | 1:45-2:45pm | Old Gym | |
| May 7 | Mon | Lacrosse vs. Newtown Friends (Away) | 3:45pm | Newtown Friends School | |
| May 8 | Tue | Lacrosse vs. Rutgers Prep (Away) | 3:45pm | Rutgers Prep | |
| May 8 | Tue | Celebration of the Arts | 7-9pm | ||
| May 9 | Wed | Tennis vs. Pingry (Home) | 3:45pm | Stuart Country Day School | |
| May 10 | Thu | Baseball vs. Rutgers Prep (Home) | 3:45pm | Smoyer Park in Princeton | |
| May 11 | Fri | Tennis vs. Cranbury (Away) | 4:00pm | Mercer County Park | |
| May 11 | Fri | Lacrosse vs. Chapin (Away) | 3:45pm | Chaping School | |
| May 11 | Fri | MS Dance-Grades 6-8 | 7-9:00pm | Stuart Country Day School of the Sacred Heart | |
| May 11 | Fri | LS Grandparents' Day | Main Building | ||
| May 12 | Sat | THE PREPPY PARTY- Princeton Academy's Annual Spring Gala | 6pm | Manor House | |
| May 14 | Mon | Lacrosse vs. Newtown Friends (Away) | 3:45pm | Newtown Friends | |
| May 15 | Tue | Tennis vs. Community Middle School (Home) | 3:45pm | Stuart Country Day School | |
| May 15 | Tue | Baseball vs. Hun (Away) | 3:30pm | Hun School | |
| May 17 | Thu | Tennis vs. Hun (Away) | 3:30pm | Hun School | |
| May 17 | Thu | Ascension Thursday Liturgy | 10am | Athletic and Convocation Center | Dress uniform required |
| May 20 | Sun | Trenton Thunder Game-7th Inning Stretch Singing | 1pm- all boys are invited to participate. Must attend 3 of 4 scheduled rehearsals: 5/8, 5/10, 5/15, 5/17. Rehearsals are at noon in the music room. Tickets to the game are $ | ||
| May 21 | Mon | Lacrosse vs. Princeton Charter (Away) | 3:45pm | Hilltop Park in Princeton | |
| May 22 | Tue | 7th Grade SSAT Flex Test | This test will be administered at Princeton Academy, during school hours | ||
| May 22 | Tue | Lacrosse vs. PDS (Away) | 4:00pm | PDS | |
| May 22 | Tue | Baseball vs. PDS (Away) | 4:00pm | PDS | |
| May 24 | Thu | Parents/Faculty Softball Game | 6:00pm | Lubas Field, Great Road, Montgomery Twp. | |
| May 28 | Mon | School Closed-Memorial Day |
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