Although none of its members have won the Stanley Cup since the adjustment , its members account for a combined 42 Stanley Cup championships ( 24 by Montreal , 13 by Toronto , and 5 by Boston ) , which is the most championships of any division in the NHL . Although none of its members have won the Stanley Cup since the realignment , its members account for a combined 42 Stanley Cup championships ( 24 by Montreal , 13 by Toronto , and 5 by Boston ) , which is the most championships of any division in the NHL .