Stanley Cup Winner 2028. The toronto maple leafs have a competitive window till 2028. In 1915, franchises began competing for the stanley cup and by 1927 the nhl was the de facto hockey league competing for the cup.

If the club can’t win a stanley cup, or multiple ones, by then toronto maple leafs fans could be looking at a long, cold rebuild. The first winner of the stanley cup was the montreal amateur athletic association (aaa), champions of the amateur hockey association of canada for 1893.