The 1999 Philadelphia Phillies season was the 117th season in the history of the franchise.
Offseason
November 5, 1998: Torey Lovullo was signed as a free agent with the Philadelphia Phillies. November 9, 1998: Paul Spoljaric was traded by the Seattle Mariners to the Philadelphia Phillies for Mark Leiter. November 19, 1998: Ricky Bottalico was traded by the Philadelphia Phillies with Garrett Stephenson to the St. Louis Cardinals for Jeff Brantley, Ron Gant, and Cliff Politte. December 22, 1998: Rob Ducey was signed as a free agent with the Philadelphia Phillies.
Regular season
The Phillies were early contenders for the wild card, going a season-high 13 games over .500 on August 6 (61–48), but injuries to pitching staff ace Curt Schilling and third baseman Scott Rolen, as well as a struggling bullpen, proved too tough to overcome. In one particularly bad stretch from August 28 to September 14, the Phillies went 1–18.
Season standings
Record vs. opponents
Transactions
May 5, 1999: Paul Spoljaric was traded by the Philadelphia Phillies to the Toronto Blue Jays for Robert Person. June 2, 1999: Brett Myers was drafted by the Philadelphia Phillies in the 1st round (12th pick) of the 1999 amateur draft. Player signed July 9, 1999. June 2, 1999: Marlon Byrd was drafted by the Philadelphia Phillies in the 10th round of the 1999 amateur draft. Player signed June 4, 1999.
1999 Game Log
|- style="background:#bfb" | 1 || April 5 || @ Braves || 7–4 || Curt Schilling (1–0) || Tom Glavine (0–1) || Jeff Brantley (1) || 47,522 || 1–0 |- style="background:#fbb" | 2 || April 6 || @ Braves || 3–11 || Greg Maddux (1–0) || Chad Ogea (0–1) || Derrin Ebert (1) || 29,183 || 1–1 |- style="background:#fbb" | 3 || April 7 || @ Braves || 0–4 || John Smoltz (1–0) || Carlton Loewer (0–1) || None || 32,164 || 1–2 |- style="background:#bfb" | 4 || April 8 || @ Braves || 6–3 || Paul Byrd (1–0) || Kevin Millwood (0–1) || Jeff Brantley (2) || 47,225 || 2–2 |- style="background:#fbb" | 5 || April 9 || @ Marlins || 4–7 || Brian Meadows (1–0) || Paul Spoljaric (0–1) || None || 13,229 || 2–3 |- style="background:#bfb" | 6 || April 10 || @ Marlins || 5–2 || Curt Schilling (2–0) || Dennis Springer (0–1) || Jeff Brantley (3) || 22,776 || 3–3 |- style="background:#bfb" | 7 || April 11 || @ Marlins || 2–1 || Chad Ogea (1–1) || Alex Fernandez (1–1) || Jeff Brantley (4) || 14,954 || 4–3 |- style="background:#fbb" | 8 || April 12 || Braves || 6–8 || Mike Cather (1–0) || Ken Ryan (0–1) || Rudy Seánez (1) || 37,582 || 4–4 |- style="background:#fbb" | 9 || April 14 || Braves || 4–10 || Kevin Millwood (1–1) || Paul Byrd (1–1) || None || 16,287 || 4–5 |- style="background:#bbb" | – || April 15 || Braves || colspan=6 | Postponed (rain); Makeup: July 23 as a traditional double-header |- style="background:#bfb" | 10 || April 16 || Marlins || 17–3 || Curt Schilling (3–0) || Dennis Springer (0–2) || None || 12,079 || 5–5 |- style="background:#bfb" | 11 || April 17 || Marlins || 2–1 || Wayne Gomes (1–0) || Antonio Alfonseca (0–1) || None || 14,817 || 6–5 |- style="background:#bfb" | 12 || April 18 || Marlins || 7–5 || Carlton Loewer (1–1) || Kirt Ojala (0–1) || None || 17,176 || 7–5 |- style="background:#fbb" | 13 || April 19 || @ Diamondbacks || 2–3 || Omar Daal (2–0) || Yorkis Pérez (0–1) || Greg Swindell (1) || 29,704 || 7–6 |- style="background:#fbb" | 14 || April 20 || @ Diamondbacks || 1–8 || Randy Johnson (2–1) || Paul Spoljaric (0–2) || None || 30,546 || 7–7 |- style="background:#fbb" | 15 || April 21 || @ Diamondbacks || 2–4 || Todd Stottlemyre (2–0) || Curt Schilling (3–1) || Gregg Olson (1) || 31,421 || 7–8 |- style="background:#bfb" | 16 || April 23 || @ Expos || 6–2 || Chad Ogea (2–1) || Dustin Hermanson (2–1) || None || 8,818 || 8–8 |- style="background:#bfb" | 17 || April 24 || @ Expos || 6–5 || Mike Grace (1–0) || Bobby Ayala (0–2) || Wayne Gomes (1) || 8,212 || 9–8 |- style="background:#bfb" | 18 || April 25 || @ Expos || 8–6 || Paul Byrd (2–1) || Ugueth Urbina (1–2) || None || 9,280 || 10–8 |- style="background:#bfb" | 19 || April 27 || Reds || 1–0 (10) || Jeff Brantley (1–0) || Gabe White (0–2) || None || 14,114 || 11–8 |- style="background:#fbb" | 20 || April 28 || Reds || 8–12 || Scott Williamson (1–1) || Jeff Brantley (1–1) || None || 12,354 || 11–9 |- style="background:#fbb" | 21 || April 29 || Reds || 3–7 || Jason Bere (2–0) || Carlton Loewer (1–2) || None || 12,248 || 11–10 |- style="background:#fbb" | 22 || April 30 || Dodgers || 3–4 || Carlos Pérez (1–3) || Paul Byrd (2–2) || Jeff Shaw (7) || 20,024 || 11–11 |-