endswith() accepts a tuple of suffixes. You can either convert your list to a tuple or just use a tuple in the first place instead of list.
In [1]: sample_str = "Chicago Blackhawks vs. New York Rangers"
In [2]: suffixes = ("Toronto Maple Leafs", "New York Rangers")
In [3]: sample_str.endswith(suffixes)
Out[3]: True
From doc:
str.endswith(suffix[, start[, end]])
Return True if the string ends with the specified suffix, otherwise return False. suffix can also be a tuple of suffixes to look for. With optional start, test beginning at that position. With optional end, stop comparing at that position.
Example:
# Check if the substring (4th to 12th character) ends with 'CEO'
S = '123456789'
x = S.endswith('45',3,5)
print(x)
# Prints True