The Jennings Cup is the longest consecutively awarded ice hockey cup in the world. Presented in 1898 by William T. Jennings for the University of Toronto interfaculty ice hockey tournament, it has been disputed every year since then. At the present, it is disputed twice a year by the men's ice hockey teams of the three campus of the University of Toronto.
In 1898 the Jennings Cup was presented to the School of Practical Science, University of Toronto, for competition in ice hockey. Its presenter, William T. Jennings, was a civil engineer, a chairman in Engineering, and a hockey enthusiast who strongly believed in athletics  . The donation of the cup brought attention to hockey at the university and stimulated an interfaculty competition. .
The first interfaculty hockey champion to win the Jennings Cup was the Applied Science Team in the year 1899–1900. Since then, the cup has been disputed every year, and today it is presented to the men's ice hockey champions of the University of Toronto Intramural tournament. Although the Stanley Cup is five years older, it was not awarded every year, in 1918–1919 to the Spanish Influenza pandemic, and recently because of the 2004–05 NHL lockout. Therefore, the Jennings Cup is the longest consecutively awarded ice hockey trophy in the world.
Jennings Cup Winners
|1929–1930||St. Michael's College|
|1930–1931||St. Michael's College|
|Year||Season||Div 1 Contact||Div 1 Non-Contact||Div 2 Non-Contact||Div 3 Non-Contact||Div 4 Non-Contact|
|2013-14||Fall||Victoria A||Architecture||SMC B|
|Winter||Skule A||Dentistry||Beta Dragons|
|Winter||St. Michael's College A||Victoria||PT/OT||UTSC||Cougars|
|2009-10||Fall||UTM B||UTSC B||Victoria||Forestry||OISE|
|Winter||St. Michael's College A||UTSC C||Law||PT/OT||OISE|
|2008-09||Fall||St. Michael's College A||Trinity||UTSC B||Medicine||New|
|Winter||St. Michael's College A||Trinity||New||Architecture||Skule|
|2007-08||Fall||St. Michael's College A||University College||UTSC B||Pharmacy||Political Animals|
|Winter||St. Michael's College A||Trinity||Rotman MBA||Biohazards||Meds B|
|2006-07||Fall||St. Michael's College A||Trinity||Meds A||LCA||Pharmacy|
|2005-06||Fall||FPEH||Trinity||UTSC C||SGS PhysChem||Pharmacy|
|Winter||St. Michael's College A||UTSC B||Victoria||Football|
|Winter||Skule A||Biohazards||Victoria B||LCA||Skule Kids|
|2003-04||Fall||Skule B||FPEH||Dentistry A||Skule Kids|
|Winter||Victoria A||FPEH||MBA||Dentistry||FPEH B|
|Winter||Victoria A||FPEH||MBA I||Dentistry A||FPEH B|
- Thomas Arthur Reed, "The Blue and White: A Record of Fifty Years of Athletic Endeavour at the University of Toronto." chapter xvi, pp. 187-210. Toronto: The University of Toronto Press, 1944 
- "UofT Intramural". Retrieved 2008-03-29.
- "Jennings Cup Winners". Archived from the original on 2011-07-06. Retrieved 2008-04-01.
- Jennings Cup - University of Toronto Intramural Athletics