The first time in the history of Milwaukee Country Day School that "a serious attempt was made to play hockey and develop some semblance of team play," according to the yearbook, The Arrow. "Be it said, however, that hockey will never be a popular sport until we are more certain of favorable skating conditions and until we arrange competitions with outside teams."

Fortunately, the school was able to obtain city water to flood an area of land near the field house, initially causing water pressure problems for the community. While the problem of ice was solved in 1919, the problem of schools and teams near the campus remained. The school relied on its inter-club games for competition.

According to the yearbook, hockey was described more as a pastime than a sport. "Any account of Country Day hockey must mention a perfectly natural lack of interest on the part of seniors due to the greater importance of basketball." The bitter cold winter of 1921-22 was good for the sport, and MCDS recorded its first game against an outside team. "This game was lost by a very one-sided score. Our opponents, who hailed from Lake Forest, were a well-balanced, well-drilled combination that displayed an astonishing knowledge of the finer points of hockey."

During this school year, the MCDS hockey team played five games against outside teams, two against Shorewood and St. John's Military Academy and one against West Allis. One game was hampered by heavy snowfall in which the puck was often lost, while the final game was described as both a water polo game and a swimming meet due to the poor ice conditions.

The earliest school picture of the MCDS hockey team was published in the 1928 yearbook.

In the 1930s, four-foot high boards were added around the rink, and a chicken-wire fence was built behind the nets. December 15 was the date when the school flooded the field each year, marking the start of the season. Team members helped put in the ice every year. Five or six players would hold up the hose to prevent it from freezing to the ground.

Game​​​​​s were not played until December 20 and, according to Tom Tuttle MCDS'45, "the hockey guys played football, then touch football, then prayed for cold weather. A February thaw was a huge problem. We always hoped the ground hog would see his shadow, guaranteeing six more weeks of winter.

The snow had to be shoveled off the ice before every practice and game. The players wore no helmets or shoulder pads, and their equipment consisted of skates, shin guards, and gloves. Loyal parents would park their cars on the hill behind the rink, and watch the games from the comfort of their heated cars, at least until the windshield became too frosted.

Hockey began to slip in popularity in the mid-1950s at MCDS, so Bill Church was contacted to help resuscitate the program. Church was a distinguished member of the faculty and one-time interim headmaster. He, along with hockey parents like Geoff Maclay, Henry Uihlein MCDS'39, Dave Wright MCDS'40, and Hobey MCDS'40 and Pate MCDS'37 Pierson, are credited with breathing new life into the program.

According to the 1959 yearbook, "A significant addition to the athletic facilities was made this year when alumni and friends of the school planned and underwrote the rebuilding of the old hockey rink. Through major donations from the Wright and Pierson families, the area was graded and new boards and a heated warming house were put up and lighting for evening skating was installed. The renovated rink was the Wright-Pierson Skating Rink. Thanks to the devotion of many people, MCDS has "one of the finest natural rinks in the state" in 1959.

It was decided that the time had come to consider artificial ice at MCDS. Several families, which had invested in a team called the Milwaukee Falcons (a forerunner to the Milwaukee Admirals), focused its energy towards the design and construction of a renovated rink at MCDS. They hired Art Nicholas, a former figurer skater and expert on artificial ice surfaces, to work on the rink. He later went on to create the present USM rink, the former Bradley Center, and assisted in the renovation of the Dartmouth College arena.

Components of the renovated rink came from a veritable who's-who of leaders in Milwaukee manufacturing. Ralph Kloppenburg prepared the architectural plans; Fred Loock, CEO of Allen Bradley Corp., donated the electrical controls; Al Silverman, president of Vilter Manufacturing, contributed two compressors which were considered the best refrigeration source for hockey ice; and Herman Ladish of the Ladish Co. donated all pipe valves and fittings.

The Ledger from the minute books shows the cost of the rink to be $76,000, most of which was raised by generous hockey families. The last $15,000 was raised in stages. A seperate fund drive was held for the roof and the planting of the trees (which still stand today) as a wind shield.

This year also marked the formation of the Milwaukee Winter Club, the first youth hockey organization, on Oct. 15, 1962. The founding directors were Harry Leadingham, Edith Maclay MDS'43, Sandy McCallum, Roland Mueller, Marion Read MDS'37, and Henry Uihlein MCDS'39.

Thanks to a generous donation from hockey parent Marge Klode, a heated warming house was built. It was used largely by MWC members and game spectators, and was a welcome addition. Previously, players and spectators used a warming shed, which was warmed by electric coil heaters. The home and away teams had to alternate time in the shed, but even the heat couldn't penetrate the leather of the popular skate at the time, the Tackaberry.

In the fall of 1964, University School of Milwaukee opened its doors on two campuses for the very first time. The merger of Milwaukee Country Day School, Milwaukee Downer Seminary, and Milwaukee University School was the first merger of three independent schools in the United States. The hockey team continued to play on the south campus rink in Whitefish Bay.

Tony Fritz began his MCDS/USM career in 1964 as a high school physical education teacher and ice hockey, soccer, and baseball coach. He is known for turning USM's fledging hockey program into a state powerhouse, compiling an overall record of 159-90-7.

​​​​​​Fritz, a native of Saskatchewan, was a rising star with the Toronto Maple Leaf's when he tragically lost an eye in a game, ending his career at 19. He wanted to continue his involvement with hockey, however, and jumped at the change to coach at MCDS a few years later. His winning attitude and camaraderie with his players quickly made MCDS/USM hockey the best in the state. In 19978, he left USM to become the head hockey coach at Lake Forest College in Illinois.

Henry Uihlein MCDS'39 and Dave Wright MCDS'40 began the first summer youth hockey camp in August 1964. They secured ice time at the Milwaukee Arena, and through connections with the Chicago Blackhawks, Wright hired three Blackhawks players to coach the Winter Club youth hockey program over three consecutive summers.

A roof was built over the south campus rink in 1965, which protected the ice from snowfall but not from snow that blew in from the northwest. The hockey team and coach Tony Fritz regularly had to shovel the south end of the rink. The rink was eventually enclosed completely in 1973.

The 1967-68 varsity boy's team held the school's best varsity record, 18-2-0, for 33 years. The team continues to hold records, such as 1,000 goals against average giving up only 19 goals all season. The team was led by senior Phil Uihlein '68 who went on to play Division 1 hockey at the University of Wisconsin and later for the Milwaukee Admirals. Standout juniors Chris Wright '69 and Robin Uihlein '69 also later played for the Badgers. Jeff Servis '69 played Division 1 hockey for St. Lawrence University.

Lowell MacDonald joined the USM staff in 1978 as the athletic director and hockey head coach after Tony Fritz left. Both of MacDonald’s sons, Lowell ’83 and Lane ’84, were accomplished high school and collegiate-level players, and both went on to lead distinguished hockey careers. Lowell went to Colgate University, where he played center for four years in the mid 1980s, and went on to play professionally in London. His brother, Lane, served as captain of Harvard University’s 1989 NCAA Championship team and was the winner of the Hobey Baker Award in 1989.

USM won the Wisconsin Independent School Athletic Association (WISAA) state hockey championship.

For the second year in a row, USM won the WISAA state championship

The north and south campuses were officially merged into one north campus in River Hills.

This was the first season played on the new Polly and Henry Uihlein Sr. Ice Arena on the River Hills campus, which was made possible thanks to generous support from Polly MDS'38 and Henry MCDS'39 Uihlein. The facility included an indoor rink, complete with locker rooms and unique amenities.

USM won the Wisconsin Independent School Athletic Association (WISAA) state hockey championship.

The first USM girl's ice hockey program was organized by Debbie Donovan, mother of Angie Donovan '96. The team competed as a club team within the Wisconsin Amateur Hockey Association. Angie went on to play for Northeastern University's 1997 Division 1 Eastern College Athletic Conference championship team.

Cal Roadhouse and Doug Coleman became co-head coaches of the varsity boy's team, becoming a powerhouse coaching duo.

During this season, the girl's team joined the Midwest Girls High School League and became USM's first varsity girls' ice hockey team. 

The USM varsity boy's hockey team joined the Wisconsin Interscholastic Athletic Association, and qualified for six consecutive state tournaments from 2001-2006.

Standout defensemen Evan Salmela '01 won the first prestigious Mr. Hockey Award, which sponsored by the Wisconsin Hockey Coaches Association and Wisconsin Hockey News. It is given to a senior who exhibits outstanding performance on the ice, high academic achievement, and who is a role model in the community.

Christine Patno, a Division 1 hockey standout from Ohio State, was hired to serve as head coach of the girls' team.

The girls' team took second place at the state tournament in the U-19 division of WAHA, while the U-16 members of the team won the state championship.

USM filed a joint application with Homestead High School, Nicolet High School, and Brown Deer High Schools with the WIAA to form a cooperative girls' hockey team under the name Milwaukee North Shore.

The varsity boy's team won its first WIAA state championship with a 8-1 win over Fond du Lac, finishing the season with 25 wins against one loss.

Whitefish Bay High School and Divine Savior Holey Angels joined the girls' co-op team, which was renamed USM Co-op.

The boy's team won its second WIAA championship, winning 5-3 over the number-one ranked team in the state, Wausau West. Co-head coaches Cal Roadhouse and Doug Coleman were named the Milwaukee Journal Sentinel Boy's Hockey Coaches of the Year.

This year's team earned the distinction of becoming the first girls' hockey team in the school's history to qualify for the WIAA state tournament in Madison, WI. Freshman goaltender Emily Wigdale '13 set a state tournament record of 51 saves in the 2-0 loss to eventual state champion River Falls Co-op.

The Wildcats girls' co-op team won their first WIAA state championship by defeating the Hayward co-op by a final of 2–1, behind goals from Sloan Sullivan '15 and Nicole Unsworth and a 27-save performance from goaltender Liz Ostermeyer '17. The Wildcats finished the season on a 15-game winning streak.

The boy's team won its third WIAA state championship with a 6-2 victory over Neenah Co-op.