There has been almost an equally long stretch of losses for the Toronto Maple Leafs Hockey team (Stanley Cup) and the England Football team (World Cup).
England issued a stamp back in 1966 when they last won the World Cup:
Here is a bit of history on the stamps which created quite an uproar back in the day:
https://www.postalmuseum.org/wp-content/uploads/2018/12/Stamp-History-1966-Winners.pdf
The Maple Leafs last won the Stanley Cup in 1967 and did not appear on a stamp until 1992 when Canada Post issued a set of three stamps commemorating the 75th Anniversary of the National Hockey League (NHL). Stamp #1444 shows the Leafs crest amongst other team crests:
It promises to be an exciting match today and may the best team win!!!