After suffering a 4-1 loss in Raleigh on Tuesday, the Detroit Red Wings were officially knocked out of the Stanley Cup Playoff race when they lost to the Carolina Hurricanes.

Many knew this was coming but now math has confirmed it. The Red Wings tried to hold it off as long as they could though. Faced with three games in three straight days the team racked up two overtime wins against Minnesota and Carolina on Sunday and Monday respectively. Their rematch with the Hurricanes on Tuesday finally did them in however.

For the first time since the 1989-1990 season the playoff bracket will not include the Red Wings. Here's how long ago that was.

George H.W. Bush was president
The world's first website and server was launched late in 1990
The first portable digital camera was sold in America
The Soviet Union voted to end its monopoly of power over its territory
The Berlin Wall's formal demolition also started this year

Of note on the Red Wings roster, Dylan Larkin (b. 1996) was still six years away from being born the last time the Red Wings weren't in the playoffs. Andreas Athanasiou and Anthony Mantha (b. 1994) were four years away from being born, and Petr Mrazek (b.1992) was two years away from being born. Defensemen Danny Dekeyser and Nick Jensen were newborns during 1990 as well.

The Reds Wings finished tied with the third longest playoff appearance streak in NHL history with 25 straight appearances.