1999 Pittsburgh Pirates season

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.
• November 18, 1998: Ricardo Rincón was traded by the Pirates to the Cleveland Indians for Brian Giles.
• December 22, 1998: Rafael Bournigal was signed as a free agent by the Pirates.
• March 27, 1999: Rafael Bournigal was released by the Pittsburgh Pirates.
• March 31, 1999: Elmer Dessens was released by the Pirates.

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 |- 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" | 101 || July 28 || @ Mets || 2–9 || Cook || Wilkins (2–1) || — || 42,920 || 49–52 |- bgcolor="ffbbbb" | 102 || July 30 || Marlins || 7–8 || Edmondson || Hansell (1–1) || Alfonseca || 25,163 || 49–53 |- bgcolor="ccffcc" | 103 || July 31 || Marlins || 4–2 || Schmidt (10–7) || Edmondson || Williams (15) || 33,862 || 50–53 |- |- bgcolor="ccffcc" | 104 || August 1 || Marlins || 2–1 || Cordova (6–5) || Fernandez || — || 19,071 || 51–53 |- bgcolor="ccffcc" | 105 || August 3 || Braves || 7–1 || Benson (9–8) || Millwood || — || 17,154 || 52–53 |- bgcolor="ccffcc" | 106 || August 4 || Braves || 3–2 || Ritchie (10–7) || Smoltz || Williams (16) || 17,625 || 53–53 |- bgcolor="ffbbbb" | 107 || August 5 || Braves || 3–6 || Remlinger || Hansell (1–2) || Rocker || 19,078 || 53–54 |- bgcolor="ccffcc" | 108 || August 6 || Cardinals || 5–1 || Anderson (1–0) || Jimenez || Silva (1) || — || 54–54 |- bgcolor="ffbbbb" | 109 || August 6 || Cardinals || 1–5 || Stephenson || Schmidt (10–8) || Croushore || 35,521 || 54–55 |- bgcolor="ccffcc" | 110 || August 7 || Cardinals || 3–1 || Cordova (7–5) || Bottenfield || Williams (17) || 41,063 || 55–55 |- bgcolor="ccffcc" | 111 || August 8 || Cardinals || 5–1 || Benson (10–8) || Oliver || — || 31,780 || 56–55 |- bgcolor="ffbbbb" | 112 || August 9 || Reds || 2–4 || Neagle || Ritchie (10–8) || Williamson || 13,423 || 56–56 |- bgcolor="ffbbbb" | 113 || August 10 || Reds || 1–6 || Guzman || Schourek (3–6) || — || 13,306 || 56–57 |- bgcolor="ccffcc" | 114 || August 11 || Reds || 5–4 || Williams (2–2) || Williamson || — || 23,728 || 57–57 |- bgcolor="ccffcc" | 115 || August 13 || @ Astros || 6–5 (13) || Clontz (1–3) || Miller || Williams (18) || 39,829 || 58–57 |- bgcolor="ffbbbb" | 116 || August 14 || @ Astros || 1–7 || Holt || Benson (10–9) || — || 44,868 || 58–58 |- bgcolor="ccffcc" | 117 || August 15 || @ Astros || 2–0 || Ritchie (11–8) || Reynolds || Williams (19) || 36,231 || 59–58 |- bgcolor="ffbbbb" | 118 || August 16 || @ Reds || 2–9 || Guzman || Schourek (3–7) || — || 19,693 || 59–59 |- bgcolor="ffbbbb" | 119 || August 17 || @ Reds || 4–7 (12) || Graves || Williams (2–3) || — || 19,118 || 59–60 |- bgcolor="ccffcc" | 120 || August 18 || @ Reds || 12–6 || Cordova (8–5) || Tomko || — || 19,733 || 60–60 |- bgcolor="ffbbbb" | 121 || August 19 || @ Reds || 0–1 || Harnisch || Benson (10–10) || Williamson || 17,904 || 60–61 |- bgcolor="ccffcc" | 122 || August 20 || Diamondbacks || 5–4 || Ritchie (12–8) || Stottlemyre || Williams (20) || 23,934 || 61–61 |- bgcolor="ffbbbb" | 123 || August 21 || Diamondbacks || 2–4 || Johnson || Anderson (1–1) || — || 31,364 || 61–62 |- bgcolor="ffbbbb" | 124 || August 22 || Diamondbacks || 5–7 || Daal || Schmidt (10–9) || Mantei || 25,112 || 61–63 |- bgcolor="ffbbbb" | 125 || August 23 || Diamondbacks || 1–2 || Reynoso || Cordova (8–6) || Mantei || 11,768 || 61–64 |- bgcolor="ffbbbb" | 126 || August 24 || Rockies || 2–3 || Leskanic || Williams (2–4) || Veres || 13,221 || 61–65 |- bgcolor="ccffcc" | 127 || August 25 || Rockies || 9–3 || Peters (2–1) || Kile || — || 12,535 || 62–65 |- bgcolor="ccffcc" | 128 || August 26 || Rockies || 8–4 || Anderson (2–1) || Astacio || — || 12,649 || 63–65 |- bgcolor="ccffcc" | 129 || August 27 || @ Giants || 4–1 || Schmidt (11–9) || Nathan || Williams (21) || 16,390 || 64–65 |- bgcolor="ffbbbb" | 130 || August 28 || @ Giants || 2–6 || Gardner || Cordova (8–7) || — || 32,783 || 64–66 |- bgcolor="ffbbbb" | 131 || August 29 || @ Giants || 3–5 || Estes || Benson (10–11) || Nen || 34,020 || 64–67 |- bgcolor="ccffcc" | 132 || August 30 || @ Rockies || 11–8 || Peters (3–1) || Ramirez || Williams (22) || 41,872 || 65–67 |- bgcolor="ccffcc" | 133 || August 31 || @ Rockies || 9–8 (10) || Williams (3–4) || Lee || Silva (2) || 41,729 || 66–67 |- |- bgcolor="ccffcc" | 134 || September 1 || @ Rockies || 9–8 || Sauerbeck (3–0) || Veres || Clontz (1) || 40,529 || 67–67 |- bgcolor="ffbbbb" | 135 || September 3 || Giants || 2–12 || Estes || Cordova (8–8) || — || 16,478 || 67–68 |- bgcolor="ffbbbb" | 136 || September 4 || Giants || 2–9 || Ortiz || Benson (10–12) || — || 19,949 || 67–69 |- bgcolor="ccffcc" | 137 || September 5 || Giants || 8–4 || Peters (4–1) || Rueter || — || 17,901 || 68–69 |- bgcolor="ffbbbb" | 138 || September 6 || Padres || 3–4 || Ashby || Ritchie (12–9) || Hoffman || 16,663 || 68–70 |- bgcolor="ccffcc" | 139 || September 7 || Padres || 3–1 || Schmidt (12–9) || Hitchcock || Silva (3) || 11,058 || 69–70 |- bgcolor="ffbbbb" | 140 || September 8 || Padres || 4–7 (10) || Hoffman || Wilkins (2–2) || — || 10,133 || 69–71 |- bgcolor="ffbbbb" | 141 || September 10 || @ Cardinals || 5–11 || Bottenfield || Benson (10–13) || — || 36,590 || 69–72 |- bgcolor="ccffcc" | 142 || September 11 || @ Cardinals || 8–5 || Peters (5–1) || Jimenez || Silva (4) || 46,011 || 70–72 |- bgcolor="ffbbbb" | 143 || September 13 || @ Diamondbacks || 1–5 || Daal || Schmidt (12–10) || Chouinard || 32,147 || 70–73 |- bgcolor="ffbbbb" | 144 || September 14 || @ Diamondbacks || 1–2 || Swindell || Wilkins (2–3) || Mantei || 30,372 || 70–74 |- bgcolor="ccffcc" | 145 || September 15 || @ Diamondbacks || 5–1 || Benson (11–13) || Reynoso || — || 31,294 || 71–74 |- bgcolor="ccffcc" | 146 || September 17 || Reds || 3–1 || Ritchie (13–9) || Villone || Sauerbeck (1) || 21,853 || 72–74 |- bgcolor="ffbbbb" | 147 || September 18 || Reds || 0–3 || Parris || Peters (5–2) || — || 21,253 || 72–75 |- bgcolor="ccffcc" | 148 || September 19 || Reds || 8–5 || Schmidt (13–10) || Harnisch || Clontz (2) || 21,183 || 73–75 |- bgcolor="ccffcc" | 149 || September 20 || Astros || 11–5 || Schourek (4–7) || Reynolds || — || 10,256 || 74–75 |- bgcolor="ffbbbb" | 150 || September 21 || Astros || 3–6 || Elarton || Benson (11–14) || Henry || 12,745 || 74–76 |- bgcolor="ccffcc" | 151 || September 22 || Astros || 3–2 || Ritchie (14–9) || Lima || — || 16,647 || 75–76 |- bgcolor="ffbbbb" | 152 || September 23 || @ Cubs || 5–8 || Bowie || Peters (5–3) || Aguilera || 36,736 || 75–77 |- bgcolor="ffbbbb" | 153 || September 24 || @ Cubs || 0–9 || Farnsworth || Schmidt (13–11) || — || 29,267 || 75–78 |- bgcolor="ffbbbb" | 154 || September 25 || @ Cubs || 1–3 || Lieber || Cordova (8–9) || — || 39,035 || 75–79 |- bgcolor="ccffcc" | 155 || September 26 || @ Cubs || 8–4 (11) || Sauerbeck (4–0) || Guthrie || — || 39,663 || 76–79 |- bgcolor="ccffcc" | 156 || September 29 || @ Brewers || 7–5 || Ritchie (15–9) || Woodard || Williams (23) || — || 77–79 |- bgcolor="ffbbbb" | 157 || September 29 || @ Brewers || 2–5 || Bere || Peters (5–4) || Wickman || 12,464 || 77–80 |- bgcolor="ccffcc" | 158 || September 30 || @ Brewers || 3–2 || Garcia (1–0) || Nomo || Sauerbeck (2) || 12,319 || 78–80 |- |- bgcolor="ffbbbb" | 159 || October 1 || @ Mets || 2–3 (11) || Mahomes || Sauerbeck (4–1) || — || 29,528 || 78–81 |- bgcolor="ffbbbb" | 160 || October 2 || @ Mets || 0–7 || Reed || Cordova (8–10) || — || 36,878 || 78–82 |- bgcolor="ffbbbb" | 161 || October 3 || @ Mets || 1–2 || Benitez || Hansell (1–3) || — || 50,111 || 78–83

Record vs. opponents

Detailed records

Roster

Opening Day lineup

Player stats

;Batting Note: G = Games played; AB = At bats; H = Hits; Avg. = Batting average; HR = Home runs; RBI = Runs batted in

;Pitching Note: G = Games pitched; IP = Innings pitched; W = Wins; L = Losses; ERA = Earned run average; SO = Strikeouts

Awards and honors

1999 Major League Baseball All-Star Game

• Ed Sprague Jr., 3B, reserve

Notable transactions

• May 17, 1999: Dale Sveum was signed as a free agent by the Pirates.
• July 23, 1999: José Guillén and Jeff Sparks were traded by the Pirates to the Tampa Bay Devil Rays for Joe Oliver and Humberto Cota.

Farm system

References

• 1999 Pittsburgh Pirates at Baseball Reference
• 1999 Pittsburgh Pirates at Baseball Almanac

References

1. From 1882–1906, the team played in [[Allegheny, Pennsylvania]], which became annexed by [[Pittsburgh]] as the [[North Side (Pittsburgh). North Side]] in 1907.
2. "Chance Sanford Stats {{!".
3. [https://www.baseball-reference.com/b/benjami01.shtml Mike Benjamin] at ''Baseball Reference''
4. [https://www.baseball-reference.com/g/gilesbr02.shtml Brian Giles] at ''Baseball Reference''
5. [https://www.baseball-reference.com/b/bournra01.shtml Rafael Bournigal] at ''Baseball Reference''
6. "Rafael Bournigal Stats {{!".
7. [https://www.baseball-reference.com/d/desseel01.shtml Elmer Dessens] at ''Baseball Reference''
8. "Major League Baseball Stats {{!}} pirates.com: Stats". Pittsburgh Pirates.
9. "Major League Baseball Stats {{!}} pirates.com: Stats". Pittsburgh Pirates.
10. [https://www.baseball-reference.com/s/sveumda01.shtml Dale Sveum] at ''Baseball Reference''
11. [https://www.baseball-reference.com/o/olivejo01.shtml Joe Oliver] at ''Baseball Reference''