Time to Celebrate!

    • HMC Class Agents 2019

    • HMC Drew 2019

The Headmaster’s Challenge tallies gifts from alumni from July through the month of February. It's a great way for Millbrook alumni to participate in a friendly competition that supports their alma mater. In 2020, alumni classes are once again competing within their decade for the highest percent participation in the Annual Fund and the ultimate goal of 44% overall participation for all Millbrook alumni.


The 2019 Headmaster's Challenge is ramping up.  Check back regularly for class standings and updates.  If you would like to celebrate the challenge with your classmates, please join us at the event in Boston.  Click the link to the right to register.  There will be a follow up Headmaster's Challenge event in NYC on April 3rd, so make sure you save the date!

2019 Headmaster's Challenge Current Standings

2018 Headmaster's Challenge Results

These are the classes to beat in 2020 - they earned victory in 2019 within their respective decades for the highest Annual Fund participation:
  • 1939, 100%
  • 1947, 60%
  • 1955, 60%
  • 1960, 55%
  • 1976, 51.35%
  • 1986, 55.81%
  • 1997 and 1992, tied with 82.35%
  • 2004, 83.02%
  • 2013, 54.67%