The National Hockey League (NHL) endured a tumultuous period of history between 1992 and 2017. It grew from 22 teams at the start of this period to 30 at the end, as the league expanded across the United States. Repeated labour conflicts interrupted play in 1992, 1994–95, 2004–05 and 2012–13; the second lockout caused the entire 2004–05 NHL season to be canceled, the first time in North American history that a sports league has canceled an entire season in a labour dispute. Nine franchises were added between 1991 and 2000, comprising the San Jose Sharks, Ottawa Senators, Tampa Bay Lightning, Florida Panthers, Mighty Ducks of Anaheim, Nashville Predators, Atlanta Thrashers, Columbus Blue Jackets and the Minnesota Wild. In addition to expansion teams, five franchises have relocated during this time: the Minnesota North Stars became the Dallas Stars (1993), the Quebec Nordiques became the Colorado Avalanche (1995), the Winnipeg Jets became the Phoenix Coyotes (1996), the Hartford Whalers became the Carolina Hurricanes (1997), and the Atlanta Thrashers became the second franchise known as the Winnipeg Jets (2011). In 1999, Wayne Gretzky retired from hockey.

Internationally, the Canada Cup gave way to the World Cup of Hockey in 1996, while NHL players first competed in the 1998 Winter Olympics. To promote itself worldwide, the NHL played regular season games in Japan in 1996, and throughout Europe since 2007. The league played its first outdoor regular season game between the Canadiens and the host Edmonton Oilers in 2003 and which led to the creation of three series of outdoor games: the Heritage Classic, Winter Classic and Stadium Series.

Increased use of defence-focused systems contributed to decreased scoring in the late 1990s, leading some to argue that the NHL's talent pool had been diluted by the 1990 expansion plan. The league has attempted several times to alter its rules to increase scoring. It began awarding teams a single point for losing in overtime in 1999, hoping to reduce the number of tie games. In 2005, ties were eliminated altogether as the penalty shootout was introduced to ensure that all games have a winner.

As the 1990s began, players were uneasy with the closeness between National Hockey League Players' Association (NHLPA) executive director Alan Eagleson and the teams' owners. As a result, Eagleson stepped down in December 1991, and was replaced by Bob Goodenow. Four years later, the Federal Bureau of Investigation indicted Eagleson on charges of racketeering, fraud, embezzlement, kickbacks and obstruction of justice over allegations that he stole millions of dollars from the NHLPA. Eagleson pleaded guilty in 1998 in a plea bargain and was fined US$1 million and sentenced to 18 months in prison. He subsequently resigned from the Hockey Hall of Fame.

Four months after replacing Eagleson, Goodenow and the NHLPA launched the first NHL strike on April 1, 1992. It lasted ten days and resulted in the players receiving larger playoff bonuses, increased control over the licensing of their likenesses and improved rights to free agency; all canceled games were also rescheduled. It also led the owners to dismiss league president John Ziegler and replace him on an interim basis with Gil Stein. Goodenow called the strike a major moment, stating "I don't think the owners took the players seriously and it wasn't until the strike that they understood the players were serious." As part of the deal, the league also agreed to have each team play two games per season for the following two years in neutral site locations, partially to help gauge markets for potential expansion.

Desiring a fresh start, Gary Bettman was installed in February 1993. Formerly a senior vice president of the National Basketball Association, Bettman became the first commissioner. He was given the task of selling the game to the American market, ending labor unrest, completing expansion plans, and modernizing the league.

The Tampa Bay Lightning and Ottawa Senators joined the league in 1992–93 as part of the owners' 1990 plan to expand the NHL to 28 teams within a decade. The Lightning made NHL history when goaltender Manon Rhéaume played a period of an exhibition game for them on September 23, 1992. Rhéaume became the first woman to play in an NHL game. She also became the first woman to sign a professional hockey contract, doing so with the Lightning's farm team, the Atlanta Knights. One year later, the Mighty Ducks of Anaheim and Florida Panthers began play as the NHL's 25th and 26th franchises. They were established as part of the NHL's attempt to regain a U.S. network television presence by expanding into southern North America. The league expected that bringing in Blockbuster Video's Wayne Huizenga to own the Panthers, and The Walt Disney Company to own the Mighty Ducks would raise its profile. The NHL's southward push continued in 1993 when the Minnesota North Stars moved to Dallas, Texas to become the Dallas Stars.

The NHL celebrated the 100th anniversary of the Stanley Cup in 1993. That year's finals featured Patrick Roy and the Montreal Canadiens against Wayne Gretzky and the Los Angeles Kings. After losing the first game, the Canadiens rallied from a late deficit to win game two in overtime after the Kings' Marty McSorley was penalized for using an illegal stick. Montreal scored on the power play, sending the game into overtime. Montreal won games three and four in overtime en route to winning the series in five games. The Canadiens won an NHL-record ten consecutive overtime games in the 1993 playoffs.