The 1999 Pittsburgh Pirates season was the 118th season of the franchise; the 113th in the National League. This was their 30th season at Three Rivers Stadium. The Pirates finished third in the National League Central with a record of 78–83.

Offseason October 15, 1998: Chance Sanford was released by the Pittsburgh Pirates. November 17, 1998: Mike Benjamin was signed as a free agent by the Pirates.Mike Benjamin at Baseball Reference November 18, 1998: Ricardo Rincón was traded by the Pirates to the Cleveland Indians for Brian Giles.Brian Giles at Baseball Reference December 22, 1998: Rafael Bournigal was signed as a free agent by the Pirates.Rafael Bournigal at Baseball Reference March 27, 1999: Rafael Bournigal was released by the Pittsburgh Pirates. March 31, 1999: Elmer Dessens was released by the Pirates.Elmer Dessens at Baseball Reference

Regular season

Season standings

Game log

|- bgcolor="ffbbbb" | 1 || April 5 || Expos || 2–9 || Hermanson || Cordova (0–1) || — || 43,405 || 0–1 |- bgcolor="ccffcc" | 2 || April 6 || Expos || 8–2 || Schmidt (1–0) || Pavano || — || 10,051 || 1–1 |- bgcolor="ffbbbb" | 3 || April 7 || Expos || 3–4 || Urbina || Loiselle (0–1) || — || 11,377 || 1–2 |- bgcolor="ccffcc" | 4 || April 9 || Cubs || 2–1 || Benson (1–0) || Sanders || Williams (1) || 19,721 || 2–2 |- bgcolor="ccffcc" | 5 || April 10 || Cubs || 9–3 || Sauerbeck (1–0) || Woodall || — || 22,479 || 3–2 |- bgcolor="ccffcc" | 6 || April 11 || Cubs || 9–6 || Schmidt (2–0) || Trachsel || — || 19,384 || 4–2 |- bgcolor="ffbbbb" | 7 || April 13 || Cardinals || 2–4 || Bottenfield || Schourek (0–1) || Acevedo || 19,724 || 4–3 |- bgcolor="ffbbbb" | 8 || April 14 || Cardinals || 5–9 || Aybar || Benson (1–1) || — || 18,780 || 4–4 |- style="text-align:center; background:#bbb;" | || April 15 || Cardinals || colspan=5 |Postponed (rain) Rescheduled for August 6 || 4–4 |- bgcolor="ffbbbb" | 9 || April 16 || @ Reds || 5–6 || Graves || Christiansen (0–1) || — || 17,974 || 4–5 |- bgcolor="ccffcc" | 10 || April 17 || @ Reds || 7–6 (10) || Christiansen (1–1) || White || — || 15,697 || 5–5 |- bgcolor="ccffcc" | 11 || April 18 || @ Reds || 4–2 || Loiselle (1–1) || Graves || Williams (2) || 16,667 || 6–5 |- bgcolor="ccffcc" | 12 || April 19 || @ Padres || 3–0 || Schourek (1–1) || Spencer || Christiansen (1) || 33,616 || 7–5 |- bgcolor="ccffcc" | 13 || April 20 || @ Padres || 7–3 (10) || Williams (1–0) || Hoffman || — || 15,439 || 8–5 |- bgcolor="ffbbbb" | 14 || April 21 || @ Padres || 0–2 || Ashby || Schmidt (2–1) || Hoffman || 13,928 || 8–6 |- bgcolor="ffbbbb" | 15 || April 23 || Brewers || 1–9 || Woodard || Peters (0–1) || — || 13,850 || 8–7 |- bgcolor="ffbbbb" | 16 || April 24 || Brewers || 3–5 || Reyes || Ritchie (0–1) || Wickman || 15,809 || 8–8 |- bgcolor="ffbbbb" | 17 || April 25 || Brewers || 2–4 || Karl || Benson (1–2) || Wickman || 17,268 || 8–9 |- bgcolor="ccffcc" | 18 || April 27 || @ Braves || 5–3 || Schmidt (3–1) || Perez || Williams (3) || 26,990 || 9–9 |- bgcolor="ffbbbb" | 19 || April 28 || @ Braves || 4–5 || Glavine || Christiansen (1–2) || — || 29,615 || 9–10 |- bgcolor="ffbbbb" | 20 || April 29 || @ Braves || 1–8 || Maddux || Silva (0–1) || — || 32,017 || 9–11 |- bgcolor="ffbbbb" | 21 || April 30 || Rockies || 2–7 || Astacio || Schourek (1–2) || — || 17,466 || 9–12

|- bgcolor="ccffcc" | 22 || May 1 || Rockies || 9–3 || Ritchie (1–1) || Wright || — || 18,599 || 10–12 |- bgcolor="ccffcc" | 23 || May 2 || Rockies || 8–5 || Schmidt (4–1) || Thomson || Williams (4) || 19,215 || 11–12 |- bgcolor="ccffcc" | 24 || May 3 || Giants || 9–8 || Loiselle (2–1) || Nen || — || 11,099 || 12–12 |- bgcolor="ffbbbb" | 25 || May 4 || Giants || 4–7 || Ortiz || Silva (0–2) || — || 10,532 || 12–13 |- bgcolor="ccffcc" | 26 || May 5 || Giants || 4–3 (12) || Loiselle (3–1) || Rodriguez || — || 14,358 || 13–13 |- bgcolor="ccffcc" | 27 || May 6 || @ Cardinals || 13–3 || Ritchie (2–1) || Osborne || — || 36,615 || 14–13 |- bgcolor="ffbbbb" | 28 || May 7 || @ Cardinals || 2–4 || Radinsky || Loiselle (3–2) || — || 39,620 || 14–14 |- bgcolor="ccffcc" | 29 || May 8 || @ Cardinals || 7–0 || Benson (2–2) || Jimenez || — || 45,790 || 15–14 |- bgcolor="ccffcc" | 30 || May 9 || @ Cardinals || 12–9 || Peters (1–1) || Aybar || Williams (5) || 45,458 || 16–14 |- bgcolor="ffbbbb" | 31 || May 10 || @ Astros || 0–6 || Hampton || Schourek (1–3) || — || 17,064 || 16–15 |- bgcolor="ffbbbb" | 32 || May 11 || @ Astros || 8–19 || Bergman || Ritchie (2–2) || — || 18,450 || 16–16 |- bgcolor="ffbbbb" | 33 || May 12 || @ Astros || 2–6 || Lima || Schmidt (4–2) || — || 19,792 || 16–17 |- bgcolor="ccffcc" | 34 || May 14 || Expos || 5–3 || Benson (3–2) || Hermanson || Williams (6) || 24,644 || 17–17 |- bgcolor="ccffcc" | 35 || May 15 || Expos || 17–6 || Silva (1–2) || Pavano || — || 27,017 || 18–17 |- bgcolor="ccffcc" | 36 || May 16 || Expos || 9–4 || Schourek (2–3) || Vazquez || — || 28,882 || 19–17 |- bgcolor="ffbbbb" | 37 || May 17 || @ Braves || 1–2 || Millwood || Ritchie (2–3) || Rocker || 30,673 || 19–18 |- bgcolor="ffbbbb" | 38 || May 18 || @ Braves || 4–12 || Perez || Schmidt (4–3) || — || 30,858 || 19–19 |- bgcolor="ffbbbb" | 39 || May 19 || @ Braves || 3–7 || Glavine || Cordova (0–2) || — || 34,106 || 19–20 |- bgcolor="ffbbbb" | 40 || May 20 || @ Marlins || 3–4 (14) || Alfonseca || Williams (1–1) || — || 11,473 || 19–21 |- bgcolor="ffbbbb" | 41 || May 21 || @ Marlins || 1–8 || Hernandez || Schourek (2–4) || — || 16,782 || 19–22 |- bgcolor="ccffcc" | 42 || May 22 || @ Marlins || 11–4 || Ritchie (3–3) || Springer || — || 23,121 || 20–22 |- bgcolor="ccffcc" | 43 || May 23 || @ Marlins || 6–5 || Wallace (1–0) || Darensbourg || Williams (7) || 19,321 || 21–22 |- bgcolor="ccffcc" | 44 || May 24 || Mets || 7–4 || Silva (2–2) || Isringhausen || Williams (8) || 11,880 || 22–22 |- bgcolor="ffbbbb" | 45 || May 25 || Mets || 3–8 || Yoshii || Benson (3–3) || — || 12,029 || 22–23 |- bgcolor="ffbbbb" | 46 || May 26 || Mets || 2–5 || Hershiser || Schourek (2–5) || Franco || 13,681 || 22–24 |- bgcolor="ccffcc" | 47 || May 28 || Astros || 6–5 || Ritchie (4–3) || Lima || Williams (9) || 17,309 || 23–24 |- bgcolor="ccffcc" | 48 || May 29 || Astros || 5–1 || Cordova (1–2) || Reynolds || — || 32,426 || 24–24 |- bgcolor="ccffcc" | 49 || May 30 || Astros || 7–3 || Benson (4–3) || Hampton || — || 28,905 || 25–24 |- bgcolor="ccffcc" | 50 || May 31 || Dodgers || 5–4 || Wilkins (1–0) || Arnold || Williams (10) || 15,924 || 26–24

|- bgcolor="ccffcc" | 51 || June 1 || Dodgers || 4–2 || Schmidt (5–3) || Valdez || Williams (11) || 10,962 || 27–24 |- bgcolor="ccffcc" | 52 || June 2 || Dodgers || 8–4 || Ritchie (5–3) || Dreifort || — || 20,807 || 28–24 |- bgcolor="ccffcc" | 53 || June 4 || @ White Sox || 6–3 (11) || Wilkins (2–0) || Simas || — || 12,238 || 29–24 |- bgcolor="ffbbbb" | 54 || June 5 || @ White Sox || 5–6 || Parque || Benson (4–4) || Foulke || 20,066 || 29–25 |- bgcolor="ffbbbb" | 55 || June 6 || @ White Sox || 3–4 || Sirotka || Silva (2–3) || Howry || 26,827 || 29–26 |- bgcolor="ffbbbb" | 56 || June 7 || @ Tigers || 4–9 || Brunson || Schmidt (5–4) || — || 14,280 || 29–27 |- bgcolor="ffbbbb" | 57 || June 8 || @ Tigers || 4–11 || Cruz || Ritchie (5–4) || — || 15,270 || 29–28 |- bgcolor="ccffcc" | 58 || June 9 || @ Tigers || 15–3 || Cordova (2–2) || Moehler || — || 15,747 || 30–28 |- bgcolor="ffbbbb" | 59 || June 11 || Royals || 3–10 || Rosado || Benson (4–5) || — || 31,052 || 30–29 |- bgcolor="ccffcc" | 60 || June 12 || Royals || 9–8 || Christiansen (2–2) || Whisenant || — || 29,569 || 31–29 |- bgcolor="ccffcc" | 61 || June 13 || Royals || 8–4 || Schmidt (6–4) || Whisenant || Williams (12) || 28,261 || 32–29 |- bgcolor="ccffcc" | 62 || June 15 || @ Dodgers || 11–1 || Ritchie (6–4) || Brown || — || 26,284 || 33–29 |- bgcolor="ffbbbb" | 63 || June 16 || @ Dodgers || 5–6 || Borbon || Clontz (0–1) || Shaw || 25,384 || 33–30 |- bgcolor="ccffcc" | 64 || June 17 || @ Dodgers || 8–3 || Benson (5–5) || Park || — || 30,888 || 34–30 |- bgcolor="ffbbbb" | 65 || June 18 || @ Padres || 2–4 || Boehringer || Silva (2–4) || Hoffman || 60,799 || 34–31 |- bgcolor="ffbbbb" | 66 || June 19 || @ Padres || 4–5 || Cunnane || Schmidt (6–5) || Hoffman || 33,803 || 34–32 |- bgcolor="ffbbbb" | 67 || June 20 || @ Padres || 3–6 || Clement || Ritchie (6–5) || Hoffman || 25,819 || 34–33 |- bgcolor="ffbbbb" | 68 || June 22 || @ Phillies || 2–3 || Wolf || Cordova (2–3) || Gomes || 18,835 || 34–34 |- bgcolor="ccffcc" | 69 || June 23 || @ Phillies || 8–6 || Benson (6–5) || Byrd || Williams (13) || 20,256 || 35–34 |- bgcolor="ffbbbb" | 70 || June 24 || @ Phillies || 5–7 || Schilling || Silva (2–5) || Gomes || 25,848 || 35–35 |- bgcolor="ccffcc" | 71 || June 25 || @ Brewers || 5–3 || Schmidt (7–5) || Abbott || Christiansen (2) || 23,958 || 36–35 |- bgcolor="ffbbbb" | 72 || June 26 || @ Brewers || 4–7 || Nomo || Ritchie (6–6) || Wickman || 26,590 || 36–36 |- bgcolor="ccffcc" | 73 || June 27 || @ Brewers || 6–5 || Cordova (3–3) || Karl || Christiansen (3) || 23,788 || 37–36 |- bgcolor="ccffcc" | 74 || June 28 || Phillies || 3–2 (10) || Hansell (1–0) || Montgomery || — || 14,144 || 38–36 |- bgcolor="ffbbbb" | 75 || June 29 || Phillies || 4–7 || Schilling || Silva (2–6) || — || 16,343 || 38–37 |- bgcolor="ccffcc" | 76 || June 30 || Phillies || 9–1 || Schmidt (8–5) || Ogea || — || 14,526 || 39–37

|- bgcolor="ccffcc" | 77 || July 1 || Phillies || 12–7 || Ritchie (7–6) || Person || — || 11,174 || 40–37 |- bgcolor="ffbbbb" | 78 || July 2 || Brewers || 2–5 || Karl || Cordova (3–4) || Wickman || 20,332 || 40–38 |- bgcolor="ffbbbb" | 79 || July 3 || Brewers || 4–9 || Pulsipher || Benson (6–6) || — || 28,893 || 40–39 |- bgcolor="ffbbbb" | 80 || July 4 || Brewers || 3–4 || Weathers || Clontz (0–2) || Wickman || 16,553 || 40–40 |- bgcolor="ffbbbb" | 81 || July 5 || Cubs || 2–5 || Lieber || Schmidt (8–6) || Aguilera || 19,762 || 40–41 |- bgcolor="ccffcc" | 82 || July 6 || Cubs || 6–1 || Ritchie (8–6) || Trachsel || — || 14,367 || 41–41 |- bgcolor="ccffcc" | 83 || July 7 || Cubs || 4–1 || Cordova (4–4) || Mulholland || — || 28,258 || 42–41 |- bgcolor="ffbbbb" | 84 || July 8 || Cubs || 4–9 || Serafini || Benson (6–7) || Sanders || 17,711 || 42–42 |- bgcolor="ffbbbb" | 85 || July 9 || @ Twins || 4–5 || Radke || Silva (2–7) || Trombley || 13,427 || 42–43 |- bgcolor="ffbbbb" | 86 || July 10 || @ Twins || 4–5 || Guardado || Williams (1–2) || — || 14,865 || 42–44 |- bgcolor="ccffcc" | 87 || July 11 || @ Twins || 10–2 || Ritchie (9–6) || Mays || — || 18,587 || 43–44 |- bgcolor="ffbbbb" | 88 || July 15 || Indians || 0–2 || Colon || Schmidt (8–7) || Jackson || 39,620 || 43–45 |- bgcolor="ccffcc" | 89 || July 16 || Indians || 11–3 || Cordova (5–4) || Burba || — || 43,519 || 44–45 |- bgcolor="ccffcc" | 90 || July 17 || Indians || 13–10 || Benson (7–7) || Nagy || Williams (14) || 43,299 || 45–45 |- bgcolor="ccffcc" | 91 || July 18 || Dodgers || 6–5 (10) || Sauerbeck (2–0) || Mills || — || 23,855 || 46–45 |- bgcolor="ffbbbb" | 92 || July 19 || Dodgers || 7–12 || Dreifort || Silva (2–8) || — || 14,805 || 46–46 |- bgcolor="ffbbbb" | 93 || July 20 || Dodgers || 4–8 || Brown || Clontz (0–3) || — || 16,921 || 46–47 |- bgcolor="ffbbbb" | 94 || July 21 || @ Cubs || 1–2 || Aguilera || Christiansen (2–3) || — || 37,006 || 46–48 |- bgcolor="ffbbbb" | 95 || July 22 || @ Cubs || 3–5 || Mulholland || Benson (7–8) || Adams || 37,112 || 46–49 |- bgcolor="ffbbbb" | 96 || July 23 || @ Expos || 1–5 || Vazquez || Ritchie (9–7) || — || 7,510 || 46–50 |- bgcolor="ccffcc" | 97 || July 24 || @ Expos || 7–2 || Schourek (3–5) || Powell || — || 13,396 || 47–50 |- bgcolor="ccffcc" | 98 || July 25 || @ Expos || 6–1 || Schmidt (9–7) || Kline || — || 12,244 || 48–50 |- bgcolor="ffbbbb" | 99 || July 26 || @ Mets || 5–7 || Reed || Cordova (5–5) || Wendell || 32,010 || 48–51 |- bgcolor="ccffcc" | 100 || July 27 || @ Mets || 5–1 || Benson (8–8) || Hershiser || — || 36,337 || 49–51 |- bgcolor="ffbbbb"