I seem to recall a Caps 4OT loss against the Isles (shudder)
Oh, I certainly remember watching that game. At the time, it was the fifth-longest game in NHL history. It's now the 11th-longest, although it's still the longest Game 7. The 4OT Caps–Pittsburgh game in 1996 was the third-longest game ever when it was played, although it's now the sixth-longest due to three more recent games that each went to a fifth overtime.
The two NHL games that reached a sixth overtime were both played in the 1930s, which is significant because they didn't yet resurface the ice between periods. The ice resurfacing machine, commonly known as a Zamboni even though there are other brands on the market, was not invented until 1949 and was not used in the NHL until 1955. The alternative is to have arena staff "flood" the ice, literally flooding it with water from hoses and then squeegy it to smooth it out. But they didn't do that in the 1930s because it took too long—they only did ice maintenance between games. I can't imagine how bad the ice must have been in the ninth period! Incidentally, they used the technique of "flooding" the ice at the 2011 Heritage Classic in Calgary because the wind chill at ice level of –13°F was deemed to be too cold to use ice resurfacing machines—the concern was that the machines' weight would crack the ice in the exceptionally cold air.
Speaking of Zambonis, our nephew drives the Zamboni at the Florida Panthers' practice facility. So I guess in view of the family connection I'd like to see them win the Cup this year out of the remaining four teams.