The WIAA goes back to 1925 to determine the beginning of its boys swimming tournament program. The first meet was held at the University of Wisconsin in Madison. The meet was held indoors, according to WIAA records, because "water on the lake was too rough.''
Milwaukee West won the first championship with West Allis runner-up.
The meet was held at a variety of sites through the years, but since 1966, it has been held exclusively at UW-Madison.
Madison Memorial has won 16 team championships to lead all other programs. The Spartans also have 16 runner-up finishes. Madison West and Waukesha (before it became North, South, and West) have won 15 State championships. Seven of Waukesha's titles came in succession (1964-70). All but one came during a 17-year period from 1958-1974. Wauwatosa, before it became two schools with East and West, won nine titles. Seven of those came during an eight-year period from 1944-51. Shorewood also has nine titles, including five in a row from 1935-39 and all nine of them coming from 1933-1943. Arrowhead and McFarland have won six team championships, with all six of McFarland's coming consecutively from 2007-12. Kenosha and Whitefish Bay have won five titles.
Boys swimming and diving was conducted in a single class until 1993 when a two-division format was adopted. Verona won the first Division 2 team championship.
Only six athletes have won the same individual event four times, and Ben McDade of Monona is the only swimmer to win four titles in multiple events. He's a four-time champion in both the 200 and 500 freestyles (2015-18). Kyle Bubolz of Waukesha North/Kettle Moraine was the first to do it. He won the Division 1 50-yard freestyle from 2001-04. Ryan Jefferson of Edgewood accomplished the feat in the diving competition, winning the Division 2 titles from 2003-06. Alex DeLakis of Eau Claire Memorial/North was a four-time Division 1 champion in the 100 breaststroke from 2010-13. In 2015, Joe Kaszubowski of Whitefish Bay was the fourth individual to accomplish the feat, capturing his fourth title in the Division 2 diving competition. Paul DeLakis of Eau Claire Memorial/North joined the ranks of the group when he won his fourth straight 100 breaststroke title in Division 1 in 2017.
There have been 42 three-time winners in the same individual event. Of those, only four individuals have won three titles in two different individual events. John Thuerer of Rhinelander won three titles in the 200 and 400 freestyles; both Edward Garst of Wauwatosa and Tom Wanezek of Brookfield East won three titles in the 50 and 100 freestyles; Tom Shane of New Berlin Eisenhower won three 200 individual medleys and 100 butterflies.
Ben McDade of Monona Grove has won the most titles, including relays, with 15. Ryan O'Donnell of McFarland has won 14, while Ben Anderson of Arrowhead, Jay Mortenson of Madison West, Tom Wanezek of Brookfield East and Paul DeLakis of Eau Claire Memorial/North have won 10. Chris Richard of Sturgeon Bay/Southern Door and Truman teDuits of Edgewood have won nine titles.
Madison Memorial has won the most State event titles with 89, Waukesha, before it split into three schools, recorded 77 individual and relay championships. Madison West has had 75 champions. Wauwatosa crowned 61 champs before forming separate programs.