The 1999 Calder Cup Playoffs of the American Hockey League began on April 21, 1999. The sixteen teams that qualified, eight from each conference, played best-of-5 series for division semifinals and best-of-7 series for division finals and conference finals. The conference champions played a best-of-7 series for the Calder Cup. The Calder Cup Final ended on June 13, 1999 with the Providence Bruins defeating the Rochester Americans four games to one to win the first Calder Cup in team history. Providence's Peter Ferraro won the Jack A. Butterfield Trophy as AHL playoff MVP.
After the 1998-99 AHL regular season, 16 teams qualified for the playoffs. The top four teams from each division qualified for the playoffs. However, due to the uneven number of teams in the Western Conference, it was possible for the fifth-placed team in the Empire Division to crossover to the Mid-Atlantic Division. This could only happen if the fifth-placed team in the Empire Division earned more points than the fourth-placed team in the Mid-Atlantic Division. In this case, the fifth-placed team from the Empire Division would play in place of the fourth-placed team from the Mid-Atlantic Division in that part of the playoff bracket. The Providence Bruins were the Eastern Conference regular season champions as well as the Macgregor Kilpatrick Trophy winners with the best overall regular season record. The Rochester Americans were the Western Conference regular season champions.
In each round the team that earned more points during the regular season receives home ice advantage, meaning they receive the "extra" game on home-ice if the series reaches the maximum number of games. There is no set series format due to arena scheduling conflicts and travel considerations.
Division Semifinals[]
Note 1: All times are in Eastern Time (UTC-4).
Note 2: Game times in italics signify games to be played only if necessary.
Note 3: Home team is listed first.
Eastern Conference[]
Atlantic Division[]
(A1) Lowell Lock Monsters vs. (A4) Saint John Flames[]
April 23
Lowell Lock Monsters
2 - 4
Saint John Flames
Tsongas Arena
April 24
Lowell Lock Monsters
3 - 4
OT
Saint John Flames
Tsongas Arena
April 28
Saint John Flames
6 - 4
Lowell Lock Monsters
Harbour Station
Saint John won series 3 – 0
(A2) St. John's Maple Leafs vs. (A3) Fredericton Canadiens[]
April 23
St. John's Maple Leafs
4 - 7
Fredericton Canadiens
Memorial Stadium (St. John's)
April 25
St. John's Maple Leafs
2 - 4
Fredericton Canadiens
Memorial Stadium (St. John's)
April 27
Fredericton Canadiens
2 - 3
OT
St. John's Maple Leafs
Aitken Centre
April 29
Fredericton Canadiens
1 - 2
St. John's Maple Leafs
Aitken Centre
May 1
St. John's Maple Leafs
2 - 3
Fredericton Canadiens
Memorial Stadium (St. John's)
Fredericton won series 3 - 2
New England Division[]
(N1) Providence Bruins vs. (N4) Worcester IceCats[]
April 23
Providence Bruins
4 - 1
Worcester IceCats
Dunkin' Donuts Center
April 24
Providence Bruins
3 - 1
Worcester IceCats
Dunkin' Donuts Center
April 30
Worcester IceCats
5 - 3
Providence Bruins
DCU Center
May 1
Worcester IceCats
3 - 6
Providence Bruins
DCU Center
Providence won series 3 – 1
(N2) Hartford Wolf Pack vs. (N3) Springfield Falcons[]
April 23
Hartford Wolf Pack
2 - 1
Springfield Falcons
XL Center
April 24
Hartford Wolf Pack
5 - 2
Springfield Falcons
XL Center
April 30
Springfield Falcons
2 - 6
Hartford Wolf Pack
MassMutual Center
Hartford won series 3 - 0
Western Conference[]
Empire Division[]
(E1) Rochester Americans vs. (E4) Adirondack Red Wings[]
April 21
Rochester Americans
3 - 2
OT
Adirondack Red Wings
Blue Cross Arena
April 23
Rochester Americans
5 - 2
Adirondack Red Wings
Blue Cross Arena
April 24
Adirondack Red Wings
1 - 2
Rochester Americans
Glens Falls Civic Center
Rochester won series 3 - 0
(E2) Albany River Rats vs. (E3) Hamilton Bulldogs[]
April 22
Syracuse Crunch
3 - 4
Hamilton Bulldogs
Times Union Center
April 24
Syracuse Crunch
3 - 2
Hamilton Bulldogs
Times Union Center
April 28
Hamilton Bulldogs
4 - 3
Syracuse Crunch
Copps Coliseum
April 30
Hamilton Bulldogs
2 - 3
Syracuse Crunch
Copps Coliseum
May 1
Syracuse Crunch
2 - 3
2OT
Hamilton Bulldogs
Times Union Center
Hamilton won series 3 - 2
Mid-Atlantic Division[]
(M1) Philadelphia Phantoms vs. (M4) Cincinnati Mighty Ducks[]
April 22
Philadelphia Phantoms
4 - 3
Cincinnati Mighty Ducks
Wachovia Center
April 24
Philadelphia Phantoms
5 - 2
Cincinnati Mighty Ducks
Wachovia Center
April 25
Cincinnati Mighty Ducks
2 - 5
Philadelphia Phantoms
Cincinnati Gardens
Philadelphia won series 3 - 0
(M2) Kentucky Thoroughblades vs. (M3) Hershey Bears[]
April 23
Kentucky Thoroughblades
2 - 3
Hershey Bears
Rupp Arena
April 24
Kentucky Thoroughblades
5 - 3
Hershey Bears
Rupp Arena
April 28
Hershey Bears
0 - 2
Kentucky Thoroughblades
Hersheypark Arena
April 30
Hershey Bears
4 - 2
Kentucky Thoroughblades
Hersheypark Arena
May 2
Kentucky Thoroughblades
2 - 0
Hershey Bears
Rupp Arena
Kentucky won series 3 - 2
Division Finals[]
Eastern Conference[]
Atlantic Division[]
(A3) Fredericton Canadiens vs. (A4) Saint John Flames[]
May 5
Fredericton Canadiens
5 - 2
Saint John Flames
Aitken Centre
May 7
Fredericton Canadiens
6 - 4
Saint John Flames
Aitken Centre
May 9
Saint John Flames
3 - 7
Fredericton Canadiens
Harbour Station
May 12
Saint John Flames
2 - 5
Fredericton Canadiens
Harbour Station
Saint John won series 4 - 0
New England Division[]
(N1) Providence Bruins vs. (N2) Hartford Wolf Pack[]
May 5
Providence Bruins
5 - 4
2OT
Hartford Wolf Pack
Dunkin' Donuts Center
May 7
Providence Bruins
5 - 3
Hartford Wolf Pack
Dunkin' Donuts Center
May 8
Hartford Wolf Pack
4 - 5
OT
Providence Bruins
XL Center
May 10
Hartford Wolf Pack
1 - 2
Providence Bruins
XL Center
Providence won series 4 - 0
Western Conference[]
Empire Division[]
(E1) Rochester Americans vs. (E3) Hamilton Bulldogs[]
May 5
Rochester Americans
3 - 1
Hamilton Bulldogs
Blue Cross Arena
May 7
Rochester Americans
5 - 2
Hamilton Bulldogs
Blue Cross Arena
May 8
Hamilton Bulldogs
2 - 1
OT
Rochester Americans
Copps Coliseum
May 11
Hamilton Bulldogs
3 - 2
Rochester Americans
Copps Coliseum
May 14
Rochester Americans
3 - 1
Hamilton Bulldogs
Blue Cross Arena
May 16
Hamilton Bulldogs
2 - 4
Rochester Americans
Copps Coliseum
Rochester won series 4 - 2
Mid-Atlantic Division[]
(M1) Philadelphia Phantoms vs. (M2) Kentucky Thoroughblades[]
May 5
Philadelphia Phantoms
3 - 6
Kentucky Thoroughblades
Wachovia Spectrum
May 7
Philadelphia Phantoms
5 - 2
Kentucky Thoroughblades
Wachovia Spectrum
May 9
Kentucky Thoroughblades
2 - 1
OT
Philadelphia Phantoms
Rupp Arena
May 11
Kentucky Thoroughblades
3 - 4
OT
Philadelphia Phantoms
Rupp Arena
May 13
Kentucky Thoroughblades
3 - 2
Philadelphia Phantoms
Rupp Arena
May 15
Philadelphia Phantoms
5 - 2
Kentucky Thoroughblades
Wachovia Spectrum
May 16
Philadelphia Phantoms
9 - 3
Kentucky Thoroughblades
Wachovia Spectrum
Philadelphia won series 4 - 3
Conference finals[]
Eastern Conference[]
(N1) Providence Bruins vs. (A3) Fredericton Canadiens[]
May 19
Providence Bruins
6 - 3
Fredericton Canadiens
Dunkin' Donuts Center
May 21
Providence Bruins
6 - 3
Fredericton Canadiens
Dunkin' Donuts Center
May 23
Fredericton Canadiens
3 - 5
Providence Bruins
Aitken Centre
May 25
Fredericton Canadiens
4 - 1
Providence Bruins
Aitken Centre
May 27
Fredericton Canadiens
4 - 0
Providence Bruins
Aitken Centre
May 29
Providence Bruins
6 - 1
Fredericton Canadiens
Dunkin' Donuts Center
Providence won series 4 - 2
Western Conference[]
(E1) Rochester Americans vs. (M1) Philadelphia Phantoms[]
May 20
Philadelphia Phantoms
3 - 2
OT
Rochester Americans
Wachovia Spectrum
May 22
Philadelphia Phantoms
5 - 2
Rochester Americans
Wachovia Spectrum
May 26
Rochester Americans
3 - 0
Philadelphia Phantoms
Blue Cross Arena
May 28
Rochester Americans
6 - 1
Philadelphia Phantoms
Blue Cross Arena
May 30
Rochester Americans
2 - 1
OT
Philadelphia Phantoms
Blue Cross Arena
June 1
Philadelphia Phantoms
2 - 4
Rochester Americans
Wachovia Spectrum
Rochester won series 4 - 2
Calder Cup Final[]
(N1) Providence Bruins vs. (E1) Rochester Americans[]