The 1991-92 Washington Capitals was probably the best chance the franchise had of winning the Stanley Cup before Alex Ovechkin. The Capitals played the Penguins in the first round, one year after Pittsburgh had bounced the Caps in the second round the year before in 1991. Mario Lemieux and the Penguins won the Stanley Cup that year. The next year, the Caps had their chance at revenge. They went up 3 games to 1 in that first round series, before the Capitals collapsed. The Pens won 3 straight and would go on to win the Stanley Cup for the second year in a row.
That Capitals team was one of the best David Poile ever assembled, with names like Dino Ciccarelli, Rod Langway, Kevin Hatcher, Peter Bondra, Al Iafrate, and Dale Hunter. The Caps were big and mean and could score but were anchored by those high scoring defensemen and good goaltending from Don Beaupre. Coach Terry Murray had coached a lesser team to the conference finals in 1990, and this was their best chance to really make a deep run in the playoffs. Hopes were dashed by Mario Lemieux and the Penguins.
So, what if the Caps had won that series? The Capitals would have won the Stanely Cup in 1992.

The Penguins hardest series to win that year was that first round series against the Capitals. If Washington had found a way to win just one of those final three games, the Caps would have advanced to the second round and played the New York Rangers. The Pens won that series in 6 games, even after losing Mario Lemieux to a hand injury. The Caps would have won that series in at least 6 games. Then they would have faced the Boston Bruins in the conference finals, the team that swept the Caps out of their first conference finals appearance in 1990. Payback would have come in spades, and the Caps would have wiped the floor with the Bruins. (For the record, the Pens swept Boston that year.)
That would have pitted the Washington Capitals against the Chicago Blackhawks in the Stanley Cup Finals. The Blackhawks were no match for the Capitals that year. The Capitals were the better team during the regular season and had just outlasted the Penguins in that first round marathon series. The battle-hardened Capitals would have made mincemeat out of the lesser Blackhawks roster and lit up Ed Belfour on their way to the first Stanley Cup Championship in Washington history.
