| Date | Day | Event | Time | Location | Dress Code |
| Dec 1 | Mon | Classes Resume | |||
| Dec 1 | Mon | Advent Prayer Service | 10am | Athletic and Convocation Center | Dress uniform required |
| Dec 2 | Tue | Make-up Picture Day | 8am - noon | Manor House | Dress uniform required for school picture re-takes |
| Dec 5 | Fri | Grade 6 Game Night with Stuart at Princeton Academy | 6:30 - 8:30pm | Athletic and Convocation Center | |
| Dec 5 | Fri | First Friday Gathering: Ms. Susan Victor, Chaplain at Woman Space, speaks on the topic "Creating Peaceful Homes: Breaking the Bonds of Silence" | 9am - noon | Manor House | |
| Dec 6 | Sat | Squash Club | 9:30-10:30am | Lawrenceville Squash Courts | |
| Dec 8 | Mon | Feast of Immaculate Conception Liturgy | 10am | Athletic and Convocation Center | Dress uniform required |
| Dec 8 | Mon | Basketball (A/B) v. Trenton Charter (Home) | 3:45pm | Athletic and Convocation Center | |
| Dec 8 | Mon | Wrestling v. Rutgers Prep (Away) | 3:45pm | Rutgers Prep | |
| Dec 9 | Tue | Coffee and Conversation with the Headmaster | 8:15am | Manor House | |
| Dec 10 | Wed | Parent-Faculty Open Basketball | 6-8pm | Athletic and Convocation Center | |
| Dec 12 | Fri | Basketball (A/B) v. Rutgers Prep (Home) | 3:30pm | Athletic and Convocation Center | |
| Dec 13 | Sat | Squash Club | 9:30-10:30am | Lawrenceville Squash Courts | |
| Dec 13 | Sat | Cookies with Santa | 2-4pm | Stuart Country Day School | |
| Dec 16 | Tue | 2nd grade play | 2:30pm | LS Reading area in library | |
| Dec 17 | Wed | National Geographic Geography Bee- FINALS | 1:25pm | Library balcony | |
| Dec 18 | Thu | 12 Days of Christmas -2nd grade | 2:40pm | LS Assembly area | |
| Dec 19 | Fri | Christmas Program | 8:30am | Athletic and Convocation Center | Dress uniform required |
| Dec 19 | Fri | Christmas break begins at the conclusion of the Christmas Program | |||
| Dec 20 | Sat | Princeton Academy is closed through January 5, 2009 | |||
| Dec 22 | Mon | Christmas Break through January 5, 2009 | |||
| Dec 25 | Thu | Princeton Academy wishes all a blessed Christmas | |||
| Dec 29 | Mon | Christmas Break Continues |