# 1998–99 NHL transactions

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.

## May

| Date | | | References |
| May 29, 1998 | To Los Angeles Kingsfuture considerations | To Nashville PredatorsMarian Cisar | |
| May 30, 1998 | To Chicago BlackhawksJean-Pierre Dumont 5th-rd pick - 1998 Entry Draft (PHI - # 124 - Francis Belanger)$^1$ | To New York IslandersDmitri Nabokov | |
* 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.

## June

| Date | | |
| June 1, 1998 | To Colorado Avalanche5th-rd pick - 1999 Entry Draft (# 142 - Will Magnuson) | To Carolina HurricanesRandy Petruk |
| June 2, 1998 | To Chicago BlackhawksColin Pepperall | To New York Rangers9th-rd pick - 1999 Entry Draft (# 251 - Petter Henning) |
| June 11, 1998 | To Phoenix CoyotesLouie DeBrusk 5th-rd pick - 1998 Entry Draft (# 115 - Jay Leach) | To Tampa Bay LightningCraig Janney |
| June 16, 1998 | To Edmonton Oilersrights to Josef Beranek | To Pittsburgh PenguinsBobby Dollas Tony Hrkac |
| June 17, 1998 | To Calgary FlamesDave Roche Ken Wregget | To Pittsburgh PenguinsTodd Hlushko German Titov |
| June 18, 1998 | To Buffalo SabresKay Whitmore 2nd-rd pick - 1998 Entry Draft (# 50 - Jaroslav Kristek) 5th-rd pick - 2000 Entry Draft (CBJ - # 150 - Tyler Kolarik)$^1$ | To San Jose SharksSteve Shields 4th-rd pick - 1998 Entry Draft (# 104 - Miroslav Zalesak) |
| June 18, 1998 | To Edmonton OilersEric Fichaud | To New York IslandersMike Watt |
| June 18, 1998 | To Phoenix CoyotesJean-Francois Jomphe | To Mighty Ducks of AnaheimJim McKenzie |
| June 18, 1998 | To Washington Capitals3rd-rd pick - 1998 Entry Draft (# 59 - Todd Hornung) 2nd-rd pick - 1999 Entry Draft (# 29 - Michal Sivek) | To Tampa Bay LightningBill Ranford |
| June 18, 1998 | To New Jersey Devils4th-rd pick - 1998 Entry Draft (# 105 - Pierre Dagenais) | To Los Angeles KingsDoug Bodger |
| June 26, 1998 | To San Jose Sharks5th-rd pick - 1998 Entry Draft (PHO - # 116 - Josh Blackburn)$^2$ | To Nashville PredatorsVille Peltonen |
| June 26, 1998 | To Nashville PredatorsSergei Krivokrasov | To Chicago Blackhawksfuture considerations |
| June 26, 1998 | To St. Louis Bluesfuture considerations$^3$ | To Nashville PredatorsDarren Turcotte conditional draft pick - highest compensatory pick - 1999 Entry Draft (FLO - # 40 - Alex Auld)$^4$ or 2nd-rd pick - 2000 Entry Draft |
| June 26, 1998 | To Montreal Canadiensfuture considerations | To Nashville PredatorsSebastien Bordeleau |
| June 26, 1998 | To Calgary Flamesfuture considerations | To Nashville PredatorsJim Dowd |
| June 26, 1998 | To Nashville PredatorsDominic Roussel Jeff Staples | To Philadelphia Flyers7th-rd pick - 1998 Entry Draft (# 175 - Cam Ondrik) |
| June 26, 1998 | To Los Angeles Kingsfuture considerations | To Nashville PredatorsKimmo Timonen Jan Vopat |
| June 26, 1998 | To Colorado Avalanchefuture considerations$^5$ | To Nashville Predators5th-rd pick - 1998 Entry Draft (# 138 - Martin Beauchesne) |
| June 27, 1998 | To San Jose Sharks1st-rd pick - 1998 Entry Draft (# 3 - Brad Stuart) 2nd-rd pick - 1998 Entry Draft (# 29 - Jonathan Cheechoo) | To Nashville Predators1st-rd pick - 1998 Entry Draft (# 2 - David Legwand) 3rd-rd pick - 1998 Entry Draft (# 85 - Geoff Koch) |
| June 27, 1998 | To Toronto Maple Leafs1st-rd pick - 1998 Entry Draft (# 10 - Nik Antropov) 3rd-rd pick - 1998 Entry Draft (# 69 - Jamie Hodson) 5th-rd pick - 1998 Entry Draft (# 126 - Morgan Warren) | To Chicago Blackhawks1st-rd pick - 1998 Entry Draft (# 8 - Mark Bell) 4th-rd pick - 1998 Entry Draft (# 94 - Matthias Trattnig) |
| June 27, 1998 | To New Jersey Devils1st-rd pick - 1998 Entry Draft (# 27 - Scott Gomez) | To Dallas Stars2nd-rd pick - 1998 Entry Draft (# 39 - John Erskine) 2nd-rd pick - 1998 Entry Draft (# 57 - Tyler Bouck) |
| June 27, 1998 | To St. Louis Blues2nd-rd pick - 1998 Entry Draft (# 41 - Maxim Linnik) | To Detroit Red Wings2nd-rd pick - 1998 Entry Draft (# 55 - Ryan Barnes) 4th-rd pick - 1998 Entry Draft (# 111 - Brent Hobday) |
| June 27, 1998 | To Colorado Avalanche3rd-rd pick - 1998 Entry Draft (# 79 - Evgeny Lazarev) | To Washington Capitals4th-rd pick - 1998 Entry Draft (# 106 - Krys Barch) 4th-rd pick - 1998 Entry Draft (# 107 - Chris Corrinet) 5th-rd pick - 1998 Entry Draft (# 118 - Mike Siklenka) |
| June 27, 1998 | To New Jersey Devils3rd-rd pick - 1998 Entry Draft (# 82 - Brian Gionta) | To Edmonton Oilersrights to Fredrik Bremberg 4th-rd pick - 1998 Entry Draft (# 113 - Kristian Antila) 5th-rd pick - 1998 Entry Draft (# 144 - Oleg Smirnov) |
| June 27, 1998 | To San Jose Sharks5th-rd pick - 1999 Entry Draft (MTL - # 145 - Marc-Andre Thinel)$^6$ | To Phoenix Coyotes5th-rd pick - 1998 Entry Draft (# 116 - Josh Blackburn) |
| June 27, 1998 | To Chicago BlackhawksPaul Coffey | To Philadelphia Flyers5th-rd pick - 1998 Entry Draft (# 124 - Francis Belanger) |
| June 27, 1998 | To Colorado Avalanche6th-rd pick - 1999 Entry Draft (# 158 - Anders Lovdahl) | To Tampa Bay Lightning7th-rd pick - 1998 Entry Draft (# 194 - Oak Hewer) 8th-rd pick - 1998 Entry Draft (# 221 - Dan Hulak) 9th-rd pick - 1998 Entry Draft (# 252 - Martin Cibák) |
| June 27, 1998 | To San Jose Sharks8th-rd pick - 1999 Entry Draft (# 241 - Douglas Murray) | To Ottawa Senators8th-rd pick - 1998 Entry Draft (# 223 - Sergei Verenkin) |
| June 27, 1998 | To San Jose Sharksrights to Gary Suter | To Chicago Blackhawks9th-rd pick - 1998 Entry Draft (# 240 - Andrei Yershov) |
| June 27, 1998 | To Boston Bruins9th-rd pick - 1999 Entry Draft (# 247 - Mikko Eloranta) | To New York Islanders9th-rd pick - 1998 Entry Draft (# 250 - Radek Matějovský) |
| June 27, 1998 | To Dallas Stars9th-rd pick - 1999 Entry Draft (# 265 - Jamie Chamberlain) | To Philadelphia Flyers9th-rd pick - 1998 Entry Draft (# 258 - Sergei Skrobot) |
| June 30, 1998 | To Montreal CanadiensSylvain Blouin 6th-rd pick - 1999 Entry Draft (PHO - # 168 - Erik Lewerström)$^7$ | To New York RangersPeter Popovic |
| June 30, 1998 | To Phoenix CoyotesMike Sullivan | To Nashville Predators7th-rd pick - 1999 Entry Draft (# 205 - Kyle Kettles) |
* 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.
* 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.
* Nashville agreed to not select Jamie McLennan from Blues in 1998 NHL Expansion Draft.
* 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.
* Nashville agreed to not select certain unspecified player(s) in the 1998 NHL Expansion Draft
* 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.
* 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.

## July

| Date | | |
| July 2, 1998 | To Toronto Maple LeafsLadislav Kohn | To Calgary FlamesDavid Cooper |
| July 7, 1998 | To Los Angeles Kingsfuture considerations | To Nashville PredatorsVitali Yachmenev |
| July 9, 1998 | To Dallas StarsTony Hrkac | To Nashville Predatorsfuture considerations |
| July 14, 1998 | To Dallas StarsAaron Gavey | To Calgary FlamesBob Bassen |
| July 14, 1998 | To Nashville PredatorsPetr Sykora 3rd-rd pick - 1999 Entry Draft (EDM - # 91 - Mike Comrie)$^1$ future considerations (4th-rd pick - 1999 Entry Draft # 124 - Alexander Krevsun)$^2$ | To Detroit Red WingsDoug Brown |
| July 14, 1998 | To Calgary Flamesrights to Jan Hlavac | To New York Islandersrights to Jorgen Jonsson |
| July 17, 1998 | To Chicago BlackhawksMark Fitzpatrick 4th-rd pick - 1999 Entry Draft (MTL - # 97 - Chris Dyment)$^3$ | To Tampa Bay LightningMichal Sykora |
| July 31, 1998 | To Los Angeles KingsManny Legace | To Carolina Hurricanesfuture considerations |
* 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.
* Trade completed on June 26, 1999
* 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.

## August

| Date | | |
| August 6, 1998 | To San Jose SharksJohan Hedberg | To Philadelphia Flyers7th-rd pick - 1999 Entry Draft (# 200 - Pavel Kasparik) |
| August 7, 1998 | To Calgary Flames9th-rd pick - 2000 Entry Draft (WAS - # 289 - Bjorn Nord)$^1$ future considerations | To Washington CapitalsRick Tabaracci |
| August 11, 1998 | To Mighty Ducks of AnaheimStu Grimson Kevin Haller | To Carolina HurricanesDave Karpa 4th-rd pick - 2000 Entry Draft (ATL - # 108 - Blake Robson)$^2$ |
| August 19, 1998 | To Nashville PredatorsJeff Nelson | To Washington Capitalsfuture considerations |
| August 21, 1998 | To Chicago BlackhawksJustin Hocking | To Ottawa SenatorsBrian Felsner |
| August 25, 1998 | To Philadelphia Flyers6th-rd pick - 2000 Entry Draft (MTL - # 172 - Scott Selig)$^3$ | To New York Islandersrights to Raymond Giroux |
| August 25, 1998 | To New Jersey DevilsChris Terreri | To Chicago Blackhawksconditional pick - 1999 Entry Draft (2nd-rd - # 63 - Stephan Mokhov)$^4$ |
| August 26, 1998 | To New Jersey DevilsKen Sutton | To San Jose Sharks5th-rd pick - 1999 Entry Draft (# 155 - Niko Dimitrakos) |
* 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.
* 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.
* 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.
* Conditions of this draft pick are unknown.

## September

| Date | | | References |
| September 3, 1998 | To Los Angeles Kings3rd-rd pick - 1999 Entry Draft (# 76 - Frantisek Kaberle) | To Chicago BlackhawksDoug Zmolek | |
| September 10, 1998 | To Colorado Avalanchecash | To New York IslandersNick Beaudoin | |

## October

| Date | | |
| October 1, 1998 | To Detroit Red Wings3rd-rd pick - 2000 Entry Draft (CHI - # 74 - Igor Radulov)$^1$ | To New York RangersMike Knuble |
| October 1, 1998 | To Edmonton OilersJim Dowd Mikhail Shtalenkov | To Nashville PredatorsDrake Berehowsky Greg de Vries Eric Fichaud |
| October 5, 1998 | To Detroit Red WingsBrent Gilchrist | To Tampa Bay Lightning6th-rd pick - 1999 Entry Draft (DET - # 181 - Kent McDonell)$^2$ |
| October 5, 1998 | To Mighty Ducks of AnaheimDominic Roussel | To Nashville PredatorsChris Mason Marc Moro |
| October 5, 1998 | To Edmonton OilersDaniel Lacroix | To Philadelphia FlyersValeri Zelepukin |
| October 9, 1998 | To Mighty Ducks of Anaheimfuture considerations | To Detroit Red WingsDoug Houda |
| October 13, 1998 | To Calgary Flames3rd-rd pick - 1999 Entry Draft (NYR - # 90 - Patrick Aufiero)$^3$ | To Philadelphia Flyersrights to Ryan Bast$^4$ 8th-rd pick - 1999 Entry Draft (# 224 - David Nystrom) |
| October 14, 1998 | To Toronto Maple LeafsAlexander Karpovtsev 4th-rd pick - 1999 Entry Draft (# 108 - Mirko Murovic) | To New York RangersMathieu Schneider |
| October 15, 1998 | To Chicago Blackhawks9th-rd pick - 1999 Entry Draft (WAS - # 249 - Igor Shadilov)$^4$ | To Washington CapitalsJames Black |
| October 16, 1998 | To Washington CapitalsTom Chorske 8th-rd pick - 1999 Entry Draft (# 219 - Maxim Orlov) | To New York Islanders6th-rd pick - 1999 Entry Draft (# 163 - Björn Melin) |
| October 19, 1998 | To Vancouver CanucksTrent Klatt | To Philadelphia Flyers6th-rd pick - 2000 Entry Draft (ATL - # 178 - Jeff Dwyer)$^6$ |
| October 22, 1998 | To Los Angeles KingsRyan Bach | To Detroit Red Wingsconditional pick - 2000 Entry Draft (6th-rd - # 187 - Pär Bäcker)$^7$ |
| October 25, 1998 | To Nashville Predators3rd-rd pick - 1999 Entry Draft (COL - # 93 - Branko Radivojevič)$^8$ | To Colorado PredatorsGreg de Vries |
| October 27, 1998 | To Calgary FlamesSteve Dubinsky Jeff Shantz | To Chicago BlackhawksJamie Allison Erik Andersson Marty McInnis |
| October 27, 1998 | To Mighty Ducks of AnaheimMarty McInnis | To Chicago Blackhawks4th-rd pick - 2000 Entry Draft (WAS - # 121 - Ryan Van Buskirk)$^9$ |
| October 29, 1998 | To Los Angeles KingsEric Lacroix | To Colorado AvalancheRoman Vopat 6th-rd pick - 1999 Entry Draft (OTT - # 164 - Martin Prusek)$^{10}$ |
| October 31, 1998 | To Phoenix Coyotesfuture considerations | To Nashville PredatorsRichard Lintner Cliff Ronning |
* 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.
* 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.
* 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.
* 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.
* 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.
* 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.
* Conditions of this draft pick are unknown.
* 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.
* 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.
* 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.

## November

| Date | | |
| November 7, 1998 | To Boston BruinsKen Belanger | To New York IslandersTed Donato |
| November 10, 1998 | To Chicago BlackhawksRoman Vopat 6th-rd pick - 1999 Entry Draft (OTT - # 164 - Martin Prusek)$^1$ | To Colorado AvalancheCam Russell |
| November 11, 1998 | To Dallas StarsJeff Norton | To Nashville PredatorsAlex Hicks 5th-rd pick - 1999 Entry Draft (NYI - # 140 - Adam Johnson)$^2$ |
| November 12, 1998 | To Colorado AvalancheShjon Podein | To Philadelphia FlyersKeith Jones |
| November 13, 1998 | To New Jersey DevilsNew Jersey's option of a 3rd-rd pick – 1999 Entry Draft or 2000 Entry Draft (# 76 – Michael Rupp) | To Chicago BlackhawksBryan Muir |
| November 16, 1998 | To Montreal CanadiensJeff Hackett Alain Nasreddine Eric Weinrich 4th-rd pick - 1999 Entry Draft (# 97 - Chris Dyment) | To Chicago BlackhawksBrad Brown Dave Manson Jocelyn Thibault |
| November 17, 1998 | To Chicago BlackhawksMike Maneluk | To Philadelphia FlyersRoman Vopat |
| November 25, 1998 | To Pittsburgh PenguinsAlexei Kovalev Harry York | To New York RangersPetr Nedved Sean Pronger Chris Tamer |
| November 27, 1998 | To New York RangersStanislav Neckar | To Ottawa SenatorsBill Berg 2nd-rd pick - 1999 Entry Draft (ANA - # 44 - Jordan Leopold)$^3$ |
* 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.
* 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.
* 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.

## December

| Date | | |
| December 10, 1998 | To Mighty Ducks of Anaheim5th-rd pick - 2000 Entry Draft (# 134 - Peter Podhradsky) | To Tampa Bay LightningDrew Bannister |
| December 12, 1998 | To Tampa Bay LightningChris Gratton Mike Sillinger | To Philadelphia FlyersDaymond Langkow Mikael Renberg |
| December 15, 1998 | To Colorado AvalancheMichael Gaul | To New York IslandersTed Crowley |
| December 18, 1998 | To Buffalo Sabres2nd-rd pick - 1999 Entry Draft (# 35 - Milan Bartovic) | To Los Angeles KingsDonald Audette |
| December 28, 1998 | To Washington CapitalsEnrico Ciccone | To Tampa Bay Lightningcash |
| December 28, 1998 | To Tampa Bay LightningPetr Svoboda | To Philadelphia FlyersKarl Dykhuis |
| December 29, 1998 | To Chicago BlackhawksNelson Emerson | To Carolina HurricanesPaul Coffey |
| December 29, 1998 | To Calgary FlamesAndrei Trefilov | To Chicago Blackhawks7th-rd pick - 1999 Entry Draft (# 195 - Yorick Treille) |

## January

| Date | | |
| January 8, 1999 | To Chicago BlackhawksFrank Bialowas | To Philadelphia FlyersDennis Bonvie |
| January 9, 1999 | To Toronto Maple LeafsBryan Berard 6th-rd pick - 1999 Entry Draft (# 161 - Jan Sochor) | To New York IslandersFelix Potvin 6th-rd pick - 1999 Entry Draft (TBL - # 182 - Fedor Fedorov)$^1$ |
| January 13, 1999 | To Phoenix CoyotesJean-Jacques Daigneault | To Nashville Predatorsfuture considerations |
| January 17, 1999 | To Vancouver CanucksMike Brown Dave Gagner Ed Jovanovski Kevin Weekes option of a 1st-rd pick 1999 Entry Draft or 2000 Entry Draft (2000 - # 23 – Nathan Smith)$^2$ | To Florida PanthersPavel Bure Brad Ference Bret Hedican option of a 3rd-rd pick 1999 Entry Draft or 2000 Entry Draft (2000 - # 77 – Robert Fried)$^2$ |
| January 18, 1999 | To Tampa Bay Lightning6th-rd pick - 1999 Entry Draft (# 182 - Fedor Fedorov) | To New York IslandersCraig Janney |
| January 19, 1999 | To Calgary FlamesAndrei Nazarov | To Tampa Bay LightningMichael Nylander |
| January 26, 1999 | To Nashville PredatorsSerhiy Klymentiev | To Philadelphia Flyerscash |
| January 28, 1999 | To Mighty Ducks of Anaheim4th-rd pick - 1999 Entry Draft (# 105 - Alexander Chagodayev) | To Chicago BlackhawksJosef Marha |
| January 29, 1999 | To Edmonton OilersAlexandre Daigle | To Philadelphia FlyersAndrei Kovalenko |
| January 29, 1999 | To Edmonton OilersAlex Selivanov | To Tampa Bay LightningAlexandre Daigle |
| January 29, 1999 | To Calgary Flamesfuture considerations | To Tampa Bay LightningSami Helenius |
* 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.
* The option was at Florida's discretion.

## February

| Date | | |
| February 3, 1999 | To Edmonton OilersBrad Church | To Washington Capitalsrights to Barrie Moore |
| February 10, 1999 | To Pittsburgh Penguinsfuture considerations | To Philadelphia FlyersSean O`Brien |
| February 12, 1999 | To Los Angeles KingsSean Pronger | To New York RangersEric Lacroix |
| February 13, 1999 | To St. Louis BluesJeff Finley Geoff Smith | To New York Rangersfuture considerations (Chris Kenady)$^1$ |
| February 16, 1999 | To Toronto Maple LeafsChris McAllister | To Vancouver CanucksDarby Hendrickson |
| February 17, 1999 | To Toronto Maple LeafsDavid Nemirovsky | To Florida PanthersJeff Ware |
| February 28, 1999 | To Calgary FlamesWade Belak Rene Corbet future considerations$^2$ (rights to Robyn Regehr) (2nd-rd pick - 2000 Entry Draft # 46 - Jarret Stoll) | To Colorado AvalancheChris Dingman Theoren Fleury |
* Trade completed on February 22, 1999.
* Date of completion of the trade is unknown.

## March

* Trading Deadline: March 23, 1999
| Date | | |
| March 6, 1999 | To Carolina HurricanesAndrei Kovalenko | To Philadelphia FlyersAdam Burt |
| March 8, 1999 | To Florida Panthers6th-rd pick - 1999 Entry Draft (DAL - # 184 - Justin Cox)$^1$ | To Ottawa SenatorsViacheslav Butsayev |
| March 8, 1999 | To Phoenix CoyotesJamie Huscroft | To Vancouver Canucksfuture considerations |
| March 9, 1999 | To Montreal CanadiensScott Lachance | To New York Islanders3rd-rd pick - 1999 Entry Draft (# 78 - Mattias Weinhandl) |
| March 10, 1999 | To Montreal CanadiensDainius Zubrus 6th-rd pick – 2000 Entry Draft (# 172 – Scott Selig) Montreal's option of Philadelphia's 2nd-rd pick – 1999 Entry Draft (# 58 – Matt Carkner) or 2000 Entry Draft or the Islanders' 2nd-rd pick – 2000 Entry Draft | To Philadelphia FlyersMark Recchi |
| March 11, 1999 | To Buffalo SabresStu Barnes | To Pittsburgh PenguinsMatthew Barnaby |
| March 11, 1999 | To Phoenix CoyotesMikhail Shtalenkov | To Edmonton Oilers5th-rd pick - 2000 Entry Draft (NAS - # 154 - Matt Koalska)$^2$ |
| March 12, 1999 | To Chicago BlackhawksRadim Bičánek | To Ottawa Senators6th-rd pick - 1999 Entry Draft (# 164 - Martin Prusek) |
| March 18, 1999 | To Tampa Bay Lightningcash | To Pittsburgh PenguinsBrent Peterson |
| March 18, 1999 | To St. Louis BluesBrad Shaw 8th-rd pick - 1999 Entry Draft (# 221 - Colin Hemingway) | To Washington Capitals6th-rd pick - 1999 Entry Draft (# 175 - Kyle Clark) |
| March 19, 1999 | To New York Islanderscash | To Ottawa SenatorsChris Luongo |
| March 20, 1999 | To New York Islanders4th-rd pick - 1999 Entry Draft (PHO - # 123 - Preston Mizzi)$^3$ | To Ottawa SenatorsTed Donato |
| March 20, 1999 | To Edmonton OilersDaniel Cleary Chad Kilger Christian Laflamme Ethan Moreau Edmonton's option to swap 2nd-rd picks – 1999 Entry Draft (# 36 – Alexei Semenov) | To Chicago BlackhawksJonas Elofsson Dean McAmmond Boris Mironov Edmonton's option to swap 2nd-rd picks – 1999 Entry Draft (# 46 – Dmitri Levinsky) |
| March 20, 1999 | To Edmonton OilersTommy Salo | To New York IslandersMats Lindgren 8th-rd pick - 1999 Entry Draft (# 228 - Radek Martinek) |
| March 20, 1999 | To Tampa Bay LightningColin Forbes conditional pick - 1999 Entry Draft$^4$ (5th-rd - # 148 - Michal Lanicek) or - 2000 Entry Draft | To Philadelphia FlyersMikael Andersson Sandy McCarthy |
| March 20, 1999 | To Phoenix CoyotesRobert Reichel 3rd-rd pick - 1999 Entry Draft (# 71 - Jason Jaspers) 4th-rd pick - 1999 Entry Draft (# 123 - Preston Mizzi) | To New York IslandersBrad Isbister 3rd-rd pick - 1999 Entry Draft (# 87 - Brian Collins) |
| March 21, 1999 | To Dallas StarsBenoît Hogue conditional 6th-rd pick - 2001 Entry Draft (# 167 - Michal Blažek)$^5$ | To Tampa Bay LightningSergey Gusev |
| March 22, 1999 | To New Jersey DevilsSergei Nemchinov | To New York Islanders4th-rd pick - 1999 Entry Draft (LAK - # 125 - Daniel Johansson)$^6$ |
| March 22, 1999 | To Calgary FlamesTom Chorske | To Washington Capitals7th-rd pick – 2000 Entry Draft (LAK - # 206 - Tim Eriksson)$^7$ 9th-rd pick – 2000 Entry Draft (# 289 – Björn Nord) |
| March 23, 1999 | To Mighty Ducks of AnaheimPeter Zezel | To Vancouver Canucksfuture considerations$^8$ |
| March 23, 1999 | To Buffalo Sabres2nd-rd pick - 1999 Entry Draft (# 64 - Michael Zigomanis) | To Dallas StarsDerek Plante |
| March 23, 1999 | To Montreal Canadiens5th-rd pick – 1999 Entry Draft (# 145 – Marc-André Thinel) 1st-rd pick – 2000 Entry Draft (# 16 – Marcel Hossa) 2nd-rd pick – 2000 Entry Draft or 2001 Entry Draft (San Jose's option) (CBJ -# 53 – Kiel McLeod)$^9$ | To San Jose SharksVincent Damphousse |
| March 23, 1999 | To San Jose SharksGreg Pankewicz | To Calgary Flamescash |
| March 23, 1999 | To Chicago BlackhawksChris Murray | To Ottawa SenatorsNelson Emerson |
| March 23, 1999 | To Buffalo SabresJoe Juneau 3rd-rd pick – 1999 Entry Draft (# 73 – Tim Preston) | To Washington CapitalsAlexei Tezikov 4th-rd pick – 2000 Entry Draft (CAL - # 116 – Levente Szuper)$^{10}$ |
| March 23, 1999 | To Buffalo SabresRhett Warrener 5th-rd pick - 1999 Entry Draft (# 138 - Ryan Miller) | To Florida PanthersMike Wilson |
| March 23, 1999 | To Detroit Red WingsChris Chelios | To Chicago BlackhawksAnders Eriksson 1st-rd pick - 1999 Entry Draft (# 23 - Steve McCarthy) 1st-rd pick - 2001 Entry Draft (# 29 - Adam Munro) |
| March 23, 1999 | To Detroit Red WingsBill Ranford | To Tampa Bay Lightningconditional pick - 1999 Entry Draft$^{11}$ |
| March 23, 1999 | To Detroit Red WingsWendel Clark 6th-rd pick - 1999 Entry Draft (# 181 - Kent McDonell) | To Tampa Bay LightningKevin Hodson 2nd-rd pick - 1999 Entry Draft (# 47 - Sheldon Keefe) |
| March 23, 1999 | To Detroit Red WingsUlf Samuelsson | To New York Rangers2nd-rd pick - 1999 Entry Draft (# 59 - David Inman) 3rd-rd pick - 2000 Entry Draft (CHI - # 74 - Igor Radulov)$^{12}$ |
| March 23, 1999 | To Phoenix CoyotesStanislav Neckář | To New York RangersJason Doig 6th-rd pick - 1999 Entry Draft ([# 177 - Jay Dardis) |
| March 23, 1999 | To Calgary FlamesLee Sorochan | To New York RangersChris O'Sullivan |
| March 23, 1999 | To Edmonton OilersVladimir Vorobiev | To New York RangersKevin Brown |
| March 23, 1999 | To St. Louis BluesBlair Atcheynum | To Nashville Predators6th-rd pick - 2000 Entry Draft (# 197 - Zbyněk Irgl) |
| March 23, 1999 | To Toronto Maple Leafs4th-rd pick - 1999 Entry Draft (# 110 - Jonathan Zion) 2nd-rd pick - 2000 Entry Draft (# 51 - Kris Vernarsky) | To Edmonton OilersJason Smith |
| March 23, 1999 | To Toronto Maple LeafsYanic Perreault | To Los Angeles KingsJason Podollan 3rd-rd pick - 1999 Entry Draft (# 92 - Cory Campbell) |
| March 23, 1999 | To Colorado AvalancheSami Helenius | To Tampa Bay Lightningfuture considerations |
| March 23, 1999 | To Los Angeles KingsDave Babych 5th-rd pick - 2000 Entry Draft (# 165 - Nathan Marsters) | To Philadelphia FlyersSteve Duchesne |
| March 23, 1999 | To Washington Capitalscash | To Philadelphia FlyersCraig Berube |
| March 23, 1999 | To Montreal CanadiensJean-Francois Jomphe | To Phoenix Coyotescash |
| March 23, 1999 | To Colorado AvalancheDale Hunter 3rd-rd picks – 2000 Entry Draft (# 92 – Sergei Klyazmin) | To Washington Capitals2nd-rd pick – 1999 Entry Draft (# 31 – Charlie Stephens) or 2000 Entry Draft$^{13}$ |
* 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.
* 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.
* 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.
* Conditions of this draft pick are unknown.
* Conditions of this draft pick are unknown.
* 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.
* 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.
* Peter Zezel refuse to report and announce his retirement. The NHL nullified the trade.
* 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.
* 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.
* Conditions of this draft pick are unknown. Tampa Bay did not select a pick from this trade.
* 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.
* Conditions of this draft pick are unknown.

## April

| Date | | | References |
| April 13, 1999 | To Nashville PredatorsAndy Berenzweig | To New York Islanders4th-rd pick - 1999 Entry Draft (# 102 - Johan Halvardsson) | |