Complex sentence: The longest game in the history of the National Hockey League is played when the Montreal Maroons and Detroit Red Wings go scoreless until 16 and a half minutes into the sixth OT when Mud Bruneteau ends it at 2:25 in the morning.
Split into simpler sentences: The longest game in the history of the National Hockey League was played. The Montreal Maroons and Detroit Red Wings went scoreless until 16 and a half minutes into the sixth OT when Mud Bruneteau ends it at 2:25 in the morning.