The 1999–2000 Boston Bruins season was the team's 76th season of operation. The Bruins failed to qualify for the 2000 Stanley Cup playoffs for the first time in the expansion era, ending a 29-year playoff streak which remains (as of 2022) the longest in North American major professional sport.

Off-season
Following a second-round loss to the Buffalo Sabres the year previous, the Bruins headed into the 1999–2000 season with confidence that they could reach the playoffs for the third straight year under head coach Pat Burns. General manager Harry Sinden signed no free agents in the offseason and made no significant moves heading into the season. Goaltender Byron Dafoe was to be the starter for the third straight year following his best season in 1998–99, going 32–23–11 with a .926 save percentage.

Regular season
On February 21, 2000, Marty McSorley, playing for the Bruins, swung his stick and hit Donald Brashear in the head with seconds left in the Bruins-Vancouver Canucks game.  Brashear lost consciousness and suffered a grade 3 concussion, but not from immediate contact with the stick. The stick hit Brashear's helmet, but caused him to fall backward, and his head hit hard on the ice.

As a result of the stick incident, McSorley was charged with assault and suspended by the NHL for the remainder of the 1999–2000 season (including playoffs) missing 23 games. On October 4, 2000, a jury found McSorley guilty of assault with a weapon for his attack on Brashear. He was sentenced to 18 months probation. The trial was the first for an on-ice attack by an NHL player since 1988. After his assault conviction, his NHL suspension was extended to one full year (through February 21, 2001). This suspension was the longest in NHL history and afterwards McSorley never played in another NHL game.

During the regular season, the Bruins were the only team not to score a short-handed goal.

Final standings

Schedule and results

|-  style="text-align:center; background:#fbb;"
|1||L||October 2, 1999||1–3 || style="text-align:left;"|  Carolina Hurricanes (1999–2000) ||0–1–0–0 || 
|-  style="text-align:center; background:#fbb;"
|2||L||October 4, 1999||0–4 || style="text-align:left;"| @ Toronto Maple Leafs (1999–2000) ||0–2–0–0 || 
|-  style="text-align:center; background:#fbb;"
|3||L||October 7, 1999||3–4 || style="text-align:left;"| @ Ottawa Senators (1999–2000) ||0–3–0–0 || 
|- style="text-align:center;"
|4||T||October 9, 1999||1–1 OT|| style="text-align:left;"|  Philadelphia Flyers (1999–2000) ||0–3–1–0 || 
|- style="text-align:center;"
|5||T||October 11, 1999||3–3 OT|| style="text-align:left;"|  Colorado Avalanche (1999–2000) ||0–3–2–0 || 
|-  style="text-align:center; background:#fbb;"
|6||L||October 13, 1999||1–2 || style="text-align:left;"| @ Colorado Avalanche (1999–2000) ||0–4–2–0 || 
|- style="text-align:center;"
|7||T||October 15, 1999||2–2 OT|| style="text-align:left;"| @ Dallas Stars (1999–2000) ||0–4–3–0 || 
|-  style="text-align:center; background:#fbb;"
|8||L||October 16, 1999||1–2 || style="text-align:left;"| @ Phoenix Coyotes (1999–2000) ||0–5–3–0 || 
|- style="text-align:center;"
|9||T||October 20, 1999||2–2 OT|| style="text-align:left;"| @ Los Angeles Kings (1999–2000) ||0–5–4–0 || 
|-  style="text-align:center; background:#cfc;"
|10||W||October 23, 1999||3–1 || style="text-align:left;"| @ San Jose Sharks (1999–2000) ||1–5–4–0 || 
|-  style="text-align:center; background:#cfc;"
|11||W||October 24, 1999||3–2 || style="text-align:left;"| @ Mighty Ducks of Anaheim (1999–2000) ||2–5–4–0 || 
|-  style="text-align:center; background:#cfc;"
|12||W||October 28, 1999||7–3 || style="text-align:left;"|  Tampa Bay Lightning (1999–2000) ||3–5–4–0 || 
|-  style="text-align:center; background:#cfc;"
|13||W||October 30, 1999||3–0 || style="text-align:left;"|  Buffalo Sabres (1999–2000) ||4–5–4–0 || 
|-

|-  style="text-align:center; background:#cfc;"
|14||W||November 4, 1999||3–1 || style="text-align:left;"|  New Jersey Devils (1999–2000) ||5–5–4–0 || 
|-  style="text-align:center; background:#cfc;"
|15||W||November 6, 1999||4–2 || style="text-align:left;"|  Atlanta Thrashers (1999–2000) ||6–5–4–0 || 
|-  style="text-align:center; background:#fbb;"
|16||L||November 10, 1999||2–6 || style="text-align:left;"| @ Buffalo Sabres (1999–2000) ||6–6–4–0 || 
|-  style="text-align:center; background:#cfc;"
|17||W||November 11, 1999||4–3 OT|| style="text-align:left;"|  Toronto Maple Leafs (1999–2000) ||7–6–4–0 || 
|-  style="text-align:center; background:#cfc;"
|18||W||November 13, 1999||5–2 || style="text-align:left;"| @ New York Rangers (1999–2000) ||8–6–4–0 || 
|- style="text-align:center;"
|19||T||November 17, 1999||2–2 OT|| style="text-align:left;"| @ New Jersey Devils (1999–2000) ||8–6–5–0 || 
|-  style="text-align:center; background:#cfc;"
|20||W||November 18, 1999||5–3 || style="text-align:left;"|  New York Rangers (1999–2000) ||9–6–5–0 || 
|-  style="text-align:center; background:#fbb;"
|21||L||November 20, 1999||0–3 || style="text-align:left;"|  Washington Capitals (1999–2000) ||9–7–5–0 || 
|-  style="text-align:center; background:#cfc;"
|22||W||November 22, 1999||2–1 || style="text-align:left;"| @ Carolina Hurricanes (1999–2000) ||10–7–5–0 || 
|-  style="text-align:center; background:#cfc;"
|23||W||November 24, 1999||5–2 || style="text-align:left;"| @ Nashville Predators (1999–2000) ||11–7–5–0 || 
|- style="text-align:center;"
|24||T||November 26, 1999||2–2 OT|| style="text-align:left;"|  Vancouver Canucks (1999–2000) ||11–7–6–0 || 
|-  style="text-align:center; background:#fbb;"
|25||L||November 28, 1999||1–2 || style="text-align:left;"|  New York Islanders (1999–2000) ||11–8–6–0 || 
|-

|- style="text-align:center;"
|26||T||December 2, 1999||2–2 OT|| style="text-align:left;"| @ Washington Capitals (1999–2000) ||11–8–7–0 || 
|-  style="text-align:center; background:#fbb;"
|27||L||December 4, 1999||3–9 || style="text-align:left;"|  Chicago Blackhawks (1999–2000) ||11–9–7–0 || 
|- style="text-align:center;"
|28||T||December 9, 1999||2–2 OT|| style="text-align:left;"|  Edmonton Oilers (1999–2000) ||11–9–8–0 || 
|-  style="text-align:center; background:#fbb;"
|29||L||December 11, 1999||4–5 || style="text-align:left;"|  Detroit Red Wings (1999–2000) ||11–10–8–0 || 
|-  style="text-align:center; background:#cfc;"
|30||W||December 13, 1999||2–0 || style="text-align:left;"|  Phoenix Coyotes (1999–2000) ||12–10–8–0 || 
|-  style="text-align:center; background:#fbb;"
|31||L||December 14, 1999||2–4 || style="text-align:left;"| @ Pittsburgh Penguins (1999–2000) ||12–11–8–0 || 
|-  style="text-align:center; background:#cfc;"
|32||W||December 17, 1999||3–1 || style="text-align:left;"| @ Atlanta Thrashers (1999–2000) ||13–11–8–0 || 
|-  style="text-align:center; background:#fbb;"
|33||L||December 18, 1999||0–4 || style="text-align:left;"| @ St. Louis Blues (1999–2000) ||13–12–8–0 || 
|-  style="text-align:center; background:#fbb;"
|34||L||December 21, 1999||1–3 || style="text-align:left;"|  Nashville Predators (1999–2000) ||13–13–8–0 || 
|- style="text-align:center;"
|35||T||December 23, 1999||3–3 OT|| style="text-align:left;"|  Montreal Canadiens (1999–2000) ||13–13–9–0 || 
|-  style="text-align:center; background:#fbb;"
|36||L||December 27, 1999||0–3 || style="text-align:left;"| @ New York Islanders (1999–2000) ||13–14–9–0 || 
|-  style="text-align:center; background:#FF6F6F;"
|37||OTL||December 29, 1999||4–5 OT|| style="text-align:left;"| @ New Jersey Devils (1999–2000) ||13–14–9–1 || 
|-  style="text-align:center; background:#FF6F6F;"
|38||OTL||December 30, 1999||4–5 OT|| style="text-align:left;"| @ Ottawa Senators (1999–2000) ||13–14–9–2 || 
|-

|- style="text-align:center;"
|39||T||January 1, 2000||2–2 OT|| style="text-align:left;"|  New Jersey Devils (1999–2000) ||13–14–10–2 || 
|-  style="text-align:center; background:#cfc;"
|40||W||January 4, 2000||7–3 || style="text-align:left;"| @ New York Islanders (1999–2000) ||14–14–10–2 || 
|-  style="text-align:center; background:#fbb;"
|41||L||January 6, 2000||3–7 || style="text-align:left;"|  Carolina Hurricanes (1999–2000) ||14–15–10–2 || 
|-  style="text-align:center; background:#fbb;"
|42||L||January 8, 2000||2–5 || style="text-align:left;"|  New York Islanders (1999–2000) ||14–16–10–2 || 
|-  style="text-align:center; background:#fbb;"
|43||L||January 11, 2000||2–3 || style="text-align:left;"|  Toronto Maple Leafs (1999–2000) ||14–17–10–2 || 
|- style="text-align:center;"
|44||T||January 13, 2000||0–0 OT|| style="text-align:left;"|  Buffalo Sabres (1999–2000) ||14–17–11–2 || 
|- style="text-align:center;"
|45||T||January 15, 2000||2–2 OT|| style="text-align:left;"| @ Montreal Canadiens (1999–2000) ||14–17–12–2 || 
|- style="text-align:center;"
|46||T||January 17, 2000||3–3 OT|| style="text-align:left;"|  Atlanta Thrashers (1999–2000) ||14–17–13–2 || 
|-  style="text-align:center; background:#cfc;"
|47||W||January 19, 2000||4–3 || style="text-align:left;"| @ Atlanta Thrashers (1999–2000) ||15–17–13–2 || 
|-  style="text-align:center; background:#cfc;"
|48||W||January 20, 2000||4–2 || style="text-align:left;"| @ Tampa Bay Lightning (1999–2000) ||16–17–13–2 || 
|-  style="text-align:center; background:#FF6F6F;"
|49||OTL||January 22, 2000||3–4 OT|| style="text-align:left;"| @ Florida Panthers (1999–2000) ||16–17–13–3 || 
|-  style="text-align:center; background:#FF6F6F;"
|50||OTL||January 24, 2000||3–4 OT|| style="text-align:left;"|  Calgary Flames (1999–2000) ||16–17–13–4 || 
|-  style="text-align:center; background:#cfc;"
|51||W||January 29, 2000||1–0 || style="text-align:left;"|  Buffalo Sabres (1999–2000) ||17–17–13–4 || 
|-  style="text-align:center; background:#fbb;"
|52||L||January 31, 2000||2–4 || style="text-align:left;"|  Mighty Ducks of Anaheim (1999–2000) ||17–18–13–4 || 
|-

|- style="text-align:center;"
|53||T||February 1, 2000||4–4 OT|| style="text-align:left;"| @ Ottawa Senators (1999–2000) ||17–18–14–4 || 
|-  style="text-align:center; background:#cfc;"
|54||W||February 3, 2000||4–2 || style="text-align:left;"|  Toronto Maple Leafs (1999–2000) ||18–18–14–4 || 
|- style="text-align:center;"
|55||T||February 8, 2000||2–2 OT|| style="text-align:left;"|  Washington Capitals (1999–2000) ||18–18–15–4 || 
|-  style="text-align:center; background:#fbb;"
|56||L||February 11, 2000||2–5 || style="text-align:left;"| @ New York Rangers (1999–2000) ||18–19–15–4 || 
|-  style="text-align:center; background:#fbb;"
|57||L||February 12, 2000||1–5 || style="text-align:left;"|  Florida Panthers (1999–2000) ||18–20–15–4 || 
|- style="text-align:center;"
|58||T||February 16, 2000||3–3 OT|| style="text-align:left;"| @ Toronto Maple Leafs (1999–2000) ||18–20–16–4 || 
|-  style="text-align:center; background:#fbb;"
|59||L||February 21, 2000||2–5 || style="text-align:left;"| @ Vancouver Canucks (1999–2000) ||18–21–16–4 || 
|-  style="text-align:center; background:#fbb;"
|60||L||February 23, 2000||2–4 || style="text-align:left;"| @ Edmonton Oilers (1999–2000) ||18–22–16–4 || 
|-  style="text-align:center; background:#cfc;"
|61||W||February 25, 2000||3–0 || style="text-align:left;"| @ Washington Capitals (1999–2000) ||19–22–16–4 || 
|- style="text-align:center;"
|62||T||February 26, 2000||2–2 OT|| style="text-align:left;"| @ Pittsburgh Penguins (1999–2000) ||19–22–17–4 || 
|-  style="text-align:center; background:#fbb;"
|63||L||February 29, 2000||3–5 || style="text-align:left;"|  Ottawa Senators (1999–2000) ||19–23–17–4 || 
|-

|-  style="text-align:center; background:#fbb;"
|64||L||March 2, 2000||2–5 || style="text-align:left;"|  Montreal Canadiens (1999–2000) ||19–24–17–4 || 
|-  style="text-align:center; background:#fbb;"
|65||L||March 4, 2000||0–3 || style="text-align:left;"|  Philadelphia Flyers (1999–2000) ||19–25–17–4 || 
|-  style="text-align:center; background:#fbb;"
|66||L||March 6, 2000||1–5 || style="text-align:left;"|  Ottawa Senators (1999–2000) ||19–26–17–4 || 
|-  style="text-align:center; background:#FF6F6F;"
|67||OTL||March 8, 2000||1–2 OT|| style="text-align:left;"| @ Buffalo Sabres (1999–2000) ||19–26–17–5 || 
|-  style="text-align:center; background:#cfc;"
|68||W||March 10, 2000||5–3 || style="text-align:left;"| @ Carolina Hurricanes (1999–2000) ||20–26–17–5 || 
|-  style="text-align:center; background:#cfc;"
|69||W||March 11, 2000||5–3 || style="text-align:left;"| @ Montreal Canadiens (1999–2000) ||21–26–17–5 || 
|-  style="text-align:center; background:#FF6F6F;"
|70||OTL||March 16, 2000||4–5 OT|| style="text-align:left;"| @ Chicago Blackhawks (1999–2000) ||21–26–17–6 || 
|-  style="text-align:center; background:#cfc;"
|71||W||March 18, 2000||3–2 || style="text-align:left;"|  Pittsburgh Penguins (1999–2000) ||22–26–17–6 || 
|-  style="text-align:center; background:#fbb;"
|72||L||March 19, 2000||2–6 || style="text-align:left;"| @ Philadelphia Flyers (1999–2000) ||22–27–17–6 || 
|-  style="text-align:center; background:#cfc;"
|73||W||March 21, 2000||4–0 || style="text-align:left;"|  Tampa Bay Lightning (1999–2000) ||23–27–17–6 || 
|-  style="text-align:center; background:#fbb;"
|74||L||March 23, 2000||1–3 || style="text-align:left;"|  Florida Panthers (1999–2000) ||23–28–17–6 || 
|- style="text-align:center;"
|75||T||March 25, 2000||4–4 OT|| style="text-align:left;"|  Los Angeles Kings (1999–2000) ||23–28–18–6 || 
|-  style="text-align:center; background:#fbb;"
|76||L||March 29, 2000||3–4 || style="text-align:left;"| @ Montreal Canadiens (1999–2000) ||23–29–18–6 || 
|-  style="text-align:center; background:#fbb;"
|77||L||March 30, 2000||2–3 || style="text-align:left;"|  St. Louis Blues (1999–2000) ||23–30–18–6 || 
|-

|- style="text-align:center;"
|78||T||April 1, 2000||2–2 OT|| style="text-align:left;"|  New York Rangers (1999–2000) ||23–30–19–6 || 
|-  style="text-align:center; background:#fbb;"
|79||L||April 4, 2000||4–5 || style="text-align:left;"| @ Tampa Bay Lightning (1999–2000) ||23–31–19–6 || 
|-  style="text-align:center; background:#fbb;"
|80||L||April 5, 2000||3–6 || style="text-align:left;"| @ Florida Panthers (1999–2000) ||23–32–19–6 || 
|-  style="text-align:center; background:#fbb;"
|81||L||April 8, 2000||0–3 || style="text-align:left;"| @ Philadelphia Flyers (1999–2000) ||23–33–19–6 || 
|-  style="text-align:center; background:#cfc;"
|82||W||April 9, 2000||3–1 || style="text-align:left;"|  Pittsburgh Penguins (1999–2000) ||24–33–19–6 || 
|-

|-
| Legend:

Player statistics

Scoring
 Position abbreviations: C = Center; D = Defense; G = Goaltender; LW = Left Wing; RW = Right Wing
  = Joined team via a transaction (e.g., trade, waivers, signing) during the season. Stats reflect time with the Bruins only.
  = Left team via a transaction (e.g., trade, waivers, release) during the season. Stats reflect time with the Bruins only.

Goaltending

Awards and records

Awards

Transactions

Trades

Free agents

Signings

Waivers

Retirement

Draft picks
Boston's draft picks at the 1999 NHL Entry Draft held at the FleetCenter in Boston, Massachusetts.

Notes
 The Bruins acquired this pick as the result of a trade on June 27, 1998 that sent a ninth-round pick in 1998 to the New York Islanders in exchange for this pick.

References

Boston Bruins
Boston Bruins
Boston Bruins seasons
Boston Bruins
Boston Bruins
Bruins
Bruins