1995-1996
Cricket returns to SMUS and the following year sees the reinstatement of the Clayton Cup. Inaugurated in 1912, the Clayton Cup has been played every year, with the exception of the last 2 years of the First World War and a gap from 1976-1997.

1996-1997
SMUS badminton and field hockey teams are crowned Provincial Champions.

The 10th student from SMUS to represent Canada in debating, Kier Wilmut, went to the World Championships in England at Reading Bluecoat's School. He finished in 13th place and was a finalist in the Persuasive Speaking event.

1999-2000
Senior Biology teacher Peter Gardiner receives a Prime Minister’s Award for Teaching Excellence - Certificate of Excellence.

2000-2001
Junior School teacher Karen Dicks receives a Prime Minister’s Award for Teaching Excellence - Certificate of Achievement.

2001-2002
Head of Science and senior house parent Michael Jackson receives a Prime Minister’s Award for Teaching Excellence - Certificate of Achievement.

2002-2003
Crothall Centre for Humanities and the Arts opens.

2003-2004
In recognition of work done over the past four years by both the St. Michaels University School Streamkeepers and Shorekeepers, an environmental achievement award was presented to a few of our most dedicated volunteers by Mayor Frank Leonard at a council meeting on June 7th, 2004.

Emily Peiffer became the top Grade-nine debate student from Vancouver Island at a provincial tournament. She went on to the Nationals in Edmonton and placed first in Canada in the toughest category, Cross-Examination Style Debate. She was third overall in Canada.

2004-2005
John and Anne Schaffter Hall Music Centre (right) opens.

First stage of the Monkman Gymnasium expansion is completed.