Time to Celebrate!

    • HMC Class Agents 2019

    • HMC Drew 2019

The Headmaster’s Challenge tallies gifts from alumni from June through the month of February. It's a great way for Millbrook alumni to participate in a friendly competition that supports their alma mater. For the 2020 Headmaster's Challenge, alumni classes will once again compete within their decade for the highest percent participation in the Annual Fund.


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

The classes who earned victory within their respective decades for having the most Annual Fund participation are as follows:
  • 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%