After the Anaheim Ducks rallied from a 4–2 deficit to defeat the Dallas Stars in game six of their first-round series on April 27, 2014, an NHL record was broken for most multi-goal comebacks by all teams in the opening round, with ten.

The Detroit Red Wings earned 93 points during the regular season, losing the tiebreaker to Columbus in regulation + overtime wins (38 to 34), and entered the playoffs as the Eastern Conference's second wild card.

In game one, Pavel Datsyuk scored the only goal with 3:01 left in Detroit's 1–0 victory,[9] but Boston went on to win four straight contests to capture the series.

[11] In game four, Boston overcame a two-goal, second-period deficit, scoring three unanswered goals – including Jarome Iginla's game-winner at 13:32 of overtime to win 3–2.

Their only previous meeting was in the 2004 Eastern Conference semifinals, in which Tampa Bay swept Montreal out of the playoffs en route to their Stanley Cup victory.

[14] With Anders Lindback in the Tampa Bay net, Steven Stamkos of the Lightning scored at 13:27 of the third period to tie game one, 4–4, before Montreal's Dale Weise won it at 18:08 of overtime.

[16] At 15:38 of the second period of game three, Tampa Bay's Ryan Callahan appeared to give his team a 2–1 lead, but his goal was waved off as the officials ruled that there was contact between Alex Killorn and Price; Montreal's Brendan Gallagher then scored minutes later, and the Canadiens went on to win 3–2.

[20] Columbus then overcame a two-goal deficit in game two after Pittsburgh built their lead with Brian Gibbons scoring his first two playoff goals, including a short-handed one.

Matt Calvert then scored both a short-handed goal and then the game-winner 1:10 into double overtime to give the Blue Jackets their first playoff victory in franchise history.

Mason went on to make 37 saves out of 38 shots, and Jakub Voracek scored the game-winning goal on a power play in the second period, as Philadelphia won, 2–1.

Throughout the series, Colorado head coach Patrick Roy used his strategy of pulling goalie Semyon Varlamov for an extra attacker earlier than usual when trailing late in the third period.

[37] The Wild then only allowed 12 Colorado shots in a 2–1 win in game four, even after Roy pulled Varlamov for the extra attacker with less than three minutes left.

[38] In game five (after Roy pulled Varlamov with 2:22 left in the third period), Colorado's P. A. Parenteau's game-tying goal with 1:14 remaining was met with controversy as the Avalanche appeared to have been offside on the play, but it was never called.

Vladimir Tarasenko then tied the game on the ensuing power play, followed by Barret Jackman scoring the game-winner at 5:50 of overtime to give St. Louis a 4–3 win.

Anaheim head coach Bruce Boudreau decided to start the series with Frederik Andersen in net, who was the hotter goalie going into the postseason, rather than original Ducks starter Jonas Hiller.

[51] The series moved to Dallas for game three, where Stars goaltender Kari Lehtonen stopped all 37 Anaheim shots to earn his first playoff victory in a 3–0 win.

Anaheim then staged a comeback, first with Nick Bonino's goal with 2:10 remaining in regulation, and then Devante Smith-Pelly's score with 24 seconds left to tie the game and force overtime.

The Kings became just the fourth team in NHL playoff history (after the 1942 Toronto Maple Leafs, 1975 New York Islanders, and the 2010 Philadelphia Flyers) to come back from a 3–0 deficit to win a series 4–3.

One of the greatest rivalries in North American professional sports, this was the 34th meeting between these teams in the postseason, which is the most frequent playoff series in NHL history.

[69] However, Carey Price stopped all 26 Boston shots, and Thomas Vanek scored two goals, helping to give Montreal a 4–0 win in game six.

[79] Between games four and five, Rangers forward Martin St. Louis received the news that his mother unexpectedly died at the age of 63 due to a heart attack.

[82] Finally, Brad Richards's power play goal 7:56 into the second period proved to be the difference in the Rangers' 2–1 victory in game seven.

However, Marian Gaborik tied the game with about seven seconds remaining in regulation, then scored the game-winner 12:17 into overtime to give Los Angeles a 3–2 win.

The 20-year-old Gibson then became the youngest goalie in NHL history to record a shutout in his playoff debut, making 28 saves to give Anaheim a 2–0 win.

[92] Gibson followed up his performance by recording 39 saves out of 42 shots, and Devante Smith-Pelly scored two goals, to help give the Ducks a 4–3 win in game five.

With the Rangers holding a 2–1 lead midway through the second period of game one, New York's Chris Kreider collided with Carey Price, injuring the Montreal goaltender's knee.

New York then tied the game at 19:31 of the third period after Daniel Girardi's shot deflected of off Chris Kreider and bounced off of Montreal's Alexei Emelin's skate into the net.

[102] However, Dominic Moore scored game six's only goal late in the second period and with a 1–0 win the Rangers advanced to the Stanley Cup Finals for the first time in twenty years.

But Marian Gaborik converted Dustin Brown's rebound to tie the game in the third period, and at 5:47 of overtime Alec Martinez's wrist shot from the blue line deflected past Crawford to give the Kings a 5–4 victory and a spot in the Stanley Cup Finals, for the second time in three years.

[112] This was the first major professional sports championship final between New York City and Los Angeles since the Dodgers beat the Yankees in the 1981 World Series in a strike-shortened season.