This list is for 1998–99 NHL transactions within professional ice hockey league of players in North America. The following contains team-to-team transactions that occurred in the National Hockey League during the 1998–99 NHL season. It lists what team each player has been traded to, or claimed by, and for which players or draft picks, if applicable.

This article relies largely or entirely on a single source. (December 2023)

1. Chicago's acquired fifth-round pick went to Philadelphia as the result of a trade on June 27, 1998, that sent Paul Coffey to Chicago in exchange for a this pick.

1. Buffalo's acquired fifth-round pick went to Columbus as the result of a trade on June 23, 2000 that sent future considerations (Columbus agreed to select Geoff Sanderson and Dwayne Roloson in the 2000 NHL Expansion Draft) to Buffalo in exchange for Matt Davidson, Jean-Luc Grand-Pierre. a fifth-round pick in the 2001 Entry Draft and this pick.
2. San Jose's acquired fifth-round pick went to Phoenix as the result of a trade on June 27, 1998 that sent a fifth-round pick in the 1999 Entry Draft to San Jose in exchange for a this pick.
3. Nashville agreed to not select Jamie McLennan from Blues in 1998 NHL Expansion Draft.
4. Nashville's acquired second-round pick went to Florida as the result of a trade on June 26, 1999 that sent a second-round pick (# 45 overall) in the 1999 Entry Draft and a third-round pick in the 2000 Entry Draft to Nashville in exchange for this pick.
5. Nashville agreed to not select certain unspecified player(s) in the 1998 NHL Expansion Draft
6. San Jose's acquired fifth-round pick went to Montreal as the result of a trade on March 23, 1999 that sent Vincent Damphousse to San Jose in exchange for a first-round pick in the 2000 Entry Draft, San Jose's option of a second-round pick in the 2000 Entry Draft or 2001 Entry Draft and this pick.
7. Montreal's acquired sixth-round pick went to Phoenix as the result of a trade on June 26, 1999 that sent Jim Cummins to Montreal in exchange for this pick.

1. Nashville's acquired fourth-round pick went to Edmonton as the result of a trade on June 26, 1999, that sent Craig Millar to Nashville in exchange for this pick.
2. Trade completed on June 26, 1999
3. Chicago's acquired fourth-round pick went to Montreal as the result of a trade on November 16, 1998, that sent Brad Brown, Dave Manson and Jocelyn Thibault to Chicago in exchange for Jeff Hackett, Alain Nasreddine, Eric Weinrich and this pick.

1. Washington re-acquired this pick as the result of a trade on March 22, 1999 that sent Tom Chorske to Clagary in exchange for a seventh-round pick in the 2000 Entry Draft and this pick.
2. Carolina's acquired fourth-round pick went Atlanta as the result of a trade on June 24, 2000 that sent a fourth-round pick in the 2000 Entry Draft to Carolina in exchange for fifth and eighth-round picks along with this pick.
3. Philadelphia's acquired sixth-round pick went to Montreal as the result of a trade on March 10, 1999 that sent Mark Recchi to Philadelphia in exchange for Dainius Zubrus, Montreal's option of a second-round pick from Philadelphia in the 1999 Entry Draft or 2000 Entry Draft or a second-round pick from the Islanders in the 2000 Entry Draft and this pick.
4. Conditions of this draft pick are unknown.

1. San Jose's acquired third-round pick went to Chicago as the result of a trade on June 24, 2000 that sent a second-round pick (# 41 overall) in the 2000 Entry Draft to San Jose in exchange for a second-round pick (#49 overall) and this pick.

   Tampa Bay's acquired third-round pick went to San Jose as the result of a trade on August 4, 1999 that sent Shawn Burr, Steve Guolla, Bill Houlder and Andrei Zyuzin to Tampa Bay in exchange for Niklas Sundstrom and this pick.

   The Rangers' re-acquired pick went to Tampa Bay as the result of a trade on June 26, 1999 that sent a first-round pick in the 1999 Entry Draft to the Rangers in exchange for Dan Cloutier, Niklas Sundstrom, a first-round pick in the 2000 Entry Draft and this pick.

   The Rangers' third-round pick was re-acquired as the result of a trade on March 23, 1999 that sent Ulf Samuelsson to Detroit in exchange for a second-round pick in the 1999 Entry Draft and this pick.

2. Detroit's sixth-round pick was re-acquired as the result of a trade on March 23, 1999 that sent Kevin Hodson and a second-round pick in the 1999 Entry Draft to Tampa Bay in exchange for Wendel Clark and this pick.
3. Calgary's acquired third-round pick went to the Rangers as the result of a trade on June 26, 1999 that sent Marc Savard and a first-round pick (# 11 overall) in the 1999 Entry Draft to Calgary in exchange for the rights to Jan Hlaváč, a first-round pick (# 9 overall) in the 1999 Entry Draft and this pick.
4. This was a compromise deal to resolve a dispute between Calgary and Philadelphia after Philadelphia signed Ryan Bast as a free agent on May 18, 1998.
5. Washington's ninth-round pick was re-acquired as the result of a trade on June 26, 1999 that sent a seventh-round pick in the 2000 Entry Draft to Chicago in exchange for this pick.
6. Philadelphia's acquired sixth-round pick went to Atlanta as the result of a trade on March 14, 2000 that sent Kirby Law to Philadelphia in exchange for a sixth-round pick in the 2001 Entry Draft and this pick.
7. Conditions of this draft pick are unknown.
8. Colorado's third-round pick was re-acquired as the result of a trade on June 26, 1999 that sent two second-round picks (# 54 & 61 overall) in the 1999 Entry Draft to Nashville in exchange for a second-round pick (# 45 overall) in the 1999 Entry Draft and this pick.
9. Chicago's acquired fourth-round pick went to Washington as the result of a trade on June 25, 2000 that sent fifth and sixth-round picks in the 2000 Entry Draft to Chicago in exchange for this pick.
10. Chicago's acquired sixth-round pick went to Ottawa as the result of a trade on March 12, 1999 that sent Radim Bicanek to Chicago in exchange for this pick.

    Chicago previously acquired this pick as the result of a trade on November 10, 1998, that sent Cam Russell to Colorado in exchange for Roman Vopat and this pick.

1. Chicago's acquired sixth-round pick went to Ottawa as the result of a trade on March 12, 1999 that sent Radim Bicanek to Chicago in exchange for this pick.
2. Florida's acquired fifth-round pick went to the Islanders as the result of a trade on June 26, 1999 that sent the rights to Jiri Dopita to Florida in exchange for this pick.
3. Ottawa's acquired second-round pick went to Anaheim as the result of a trade on June 26, 1999 that sent a second-round pick (# 48 overall) and a sixth-round pick in the 1999 Entry Draft to Ottawa in exchange for this pick.

1. The Islanders' acquired sixth-round pick went to Tampa Bay as the result of a trade on January 18, 1999 that sent Craig Janney to the Islanders in exchange for this pick.
2. The option was at Florida's discretion.

1. Trade completed on February 22, 1999.
2. Date of completion of the trade is unknown.

• Trading Deadline: March 23, 1999^[106]

1. Atlanta's acquired sixth-round pick went to Dallas as the result of a trade on June 26, 1999 that sent Per Svartvadet to Atlanta in exchange for this pick.

   Atlanta previously acquired this pick as the result of a trade on June 25, 1999 that sent Trevor Kidd to Florida in exchange for Gord Murphy, Daniel Tjarnqvist, Herbert Vasiljevs and this pick.

2. Edmonton's acquired fifth-round pick went to Nashville as the result of a trade on June 12, 2000 that sent Patrick Côté to Edmonton in exchange for this pick.
3. The Islanders' acquired fourth-round pick went to Phoenix as the result of a trade on March 20, 1999 that sent Brad Isbister and a third-round pick in the 1999 Entry Draft to the Islanders in exchange for Robert Reichel, a third-round pick in the 1999 Entry Draft and this pick.
4. Conditions of this draft pick are unknown.
5. Conditions of this draft pick are unknown.
6. The Islanders' acquired fourth-round pick went to Los Angeles as the result of a trade on June 19, 1999 that sent Mathieu Biron, Josh Green, Olli Jokinen and a first-round pick in the 1999 Entry Draft to the Islanders in exchange for Marcel Cousineau, Žigmund Pálffy, Bryan Smolinski and this pick.
7. Washington's acquired seventh-round pick went to Los Angeles as the result of a trade on June 25, 2000 that sent a fifth-round pick in the 2000 Entry Draft to Washington in exchange for a seventh-round pick (# 201 overall) in the 2000 Entry Draft and this pick.
8. Peter Zezel refuse to report and announce his retirement. The NHL nullified the trade.
9. Montreal's second-round pick went to Columbus as the result of a trade on June 23, 2000, to complete an agreement that Columbus selects Frederic Chabot in the 2000 NHL Expansion Draft in exchange for this pick.
10. Washington's acquired fourth-round pick went to Calgary as the result of a trade on June 24, 2000 that sent a second-round pick in the 2000 Entry Draft to Washington in exchange for Miika Elomo and this pick.
11. Conditions of this draft pick are unknown. Tampa Bay did not select a pick from this trade.
12. San Jose's acquired third-round pick went to Chicago as the result of a trade on June 24, 2000 that sent a second-round pick (# 41 overall) in the 2000 Entry Draft to San Jose in exchange for a second-round pick (#49 overall) and this pick.

    Tampa Bay's acquired third-round pick went to San Jose as the result of a trade on August 4, 1999 that sent Shawn Burr, Steve Guolla, Bill Houlder and Andrei Zyuzin to Tampa Bay in exchange for Niklas Sundstrom and this pick.

    The Rangers' re-acquired pick went to Tampa Bay as the result of a trade on June 26, 1999 that sent a first-round pick in the 1999 Entry Draft to the Rangers in exchange for Dan Cloutier, Niklas Sundstrom, a first-round pick in the 2000 Entry Draft and this pick.

13. Conditions of this draft pick are unknown.

• 1998-99 NHL season
• 1998 NHL Entry Draft
• 1998 in sports
• 1999 in sports