The 1998–99 Chicago Blackhawks season was the 73rd season of operation of the Chicago Blackhawks in the National Hockey League. They missed the playoffs in back to back seasons for the first time since the 1957–58 season.
Offseason
Regular season
The Blackhawks allowed the most power-play goals of all 27 teams, with 80. Captain Chris Chelios was traded late in the season, to the Detroit Red Wings. The team finishes the season without a captain.
Final standings
Schedule and results
|- align="center" bgcolor="#CCFFCC" |1||W||October 10, 1998||2–1 || align="left"| New Jersey Devils (1998–99) ||1–0–0 || |- align="center" bgcolor="#FFBBBB" |2||L||October 13, 1998||1–3 || align="left"| @ Dallas Stars (1998–99) ||1–1–0 || |- align="center" bgcolor="#FFBBBB" |3||L||October 15, 1998||3–5 || align="left"| Mighty Ducks of Anaheim (1998–99) ||1–2–0 || |- align="center" bgcolor="#CCFFCC" |4||W||October 17, 1998||4–3 || align="left"| Dallas Stars (1998–99) ||2–2–0 || |- align="center" bgcolor="#CCFFCC" |5||W||October 19, 1998||2–1 || align="left"| @ Montreal Canadiens (1998–99) ||3–2–0 || |- align="center" |6||T||October 22, 1998||2–2 OT|| align="left"| San Jose Sharks (1998–99) ||3–2–1 || |- align="center" bgcolor="#CCFFCC" |7||W||October 24, 1998||5–4 || align="left"| Nashville Predators (1998–99) ||4–2–1 || |- align="center" bgcolor="#FFBBBB" |8||L||October 28, 1998||0–2 || align="left"| @ Carolina Hurricanes (1998–99) ||4–3–1 || |- align="center" bgcolor="#FFBBBB" |9||L||October 30, 1998||3–7 || align="left"| Florida Panthers (1998–99) ||4–4–1 || |-
|- align="center" bgcolor="#FFBBBB" |10||L||November 1, 1998||1–4 || align="left"| Calgary Flames (1998–99) ||4–5–1 || |- align="center" bgcolor="#FFBBBB" |11||L||November 4, 1998||1–2 || align="left"| @ Florida Panthers (1998–99) ||4–6–1 || |- align="center" |12||T||November 6, 1998||2–2 OT|| align="left"| @ Tampa Bay Lightning (1998–99) ||4–6–2 || |- align="center" bgcolor="#FFBBBB" |13||L||November 8, 1998||2–3 OT|| align="left"| Edmonton Oilers (1998–99) ||4–7–2 || |- align="center" bgcolor="#FFBBBB" |14||L||November 10, 1998||2–5 || align="left"| @ St. Louis Blues (1998–99) ||4–8–2 || |- align="center" bgcolor="#FFBBBB" |15||L||November 12, 1998||3–10 || align="left"| Toronto Maple Leafs (1998–99) ||4–9–2 || |- align="center" bgcolor="#FFBBBB" |16||L||November 14, 1998||1–6 || align="left"| @ Buffalo Sabres (1998–99) ||4–10–2 || |- align="center" |17||T||November 15, 1998||2–2 OT|| align="left"| Ottawa Senators (1998–99) ||4–10–3 || |- align="center" bgcolor="#CCFFCC" |18||W||November 17, 1998||2–1 || align="left"| @ Nashville Predators (1998–99) ||5–10–3 || |- align="center" bgcolor="#FFBBBB" |19||L||November 21, 1998||0–5 || align="left"| @ Los Angeles Kings (1998–99) ||5–11–3 || |- align="center" bgcolor="#FFBBBB" |20||L||November 22, 1998||1–4 || align="left"| @ Mighty Ducks of Anaheim (1998–99) ||5–12–3 || |- align="center" bgcolor="#FFBBBB" |21||L||November 24, 1998||2–3 || align="left"| @ Phoenix Coyotes (1998–99) ||5–13–3 || |- align="center" bgcolor="#FFBBBB" |22||L||November 28, 1998||4–5 || align="left"| @ Calgary Flames (1998–99) ||5–14–3 || |- align="center" bgcolor="#CCFFCC" |23||W||November 29, 1998||3–2 || align="left"| @ Edmonton Oilers (1998–99) ||6–14–3 || |-