July 6 || Brewers || 1–0 || Robert Person (2–4) || Hideo Nomo (6–2) || Wayne Gomes (12) || 13,006 || 44–38 |- style="background:#bfb" | 83 || July 7 || Brewers || 5–4 || Wayne Gomes (2–1) || Bob Wickman (2–4) || None || 16,593 || 45–38 |- style="background:#bfb" | 84 || July 9 || Orioles || 4–2 || Curt Schilling (13–4) || Juan Guzmán (4–7) || None || 28,182 || 46–38 |- style="background:#fbb" | 85 || July 10 || Orioles || 4–8 || Mike Mussina (11–4) || Paul Byrd (11–5) || None || 32,300 || 46–39 |- style="background:#fbb" | 86 || July 11 || Orioles || 2–6 || Scott Erickson (4–8) || Chad Ogea (4–9) || None || 33,399 || 46–40 |- style="background:#bbcaff;" | – || July 13 ||colspan="7" |1999 Major League Baseball All-Star Game at Fenway Park in Boston |- style="background:#fbb" | 87 || July 15 || @ Red Sox || 4–6 || Brian Rose (5–2) || Paul Byrd (11–6) || Tim Wakefield (11) || 32,397 || 46–41 |- style="background:#bfb" | 88 || July 16 || @ Red Sox || 5–4 || Robert Person (3–4) || Bret Saberhagen (6–3) || Wayne Gomes (13) || 32,899 || 47–41 |- style="background:#bfb" | 89 || July 17 || @ Red Sox || 11–3 || Randy Wolf (5–0) || Mark Portugal (5–7) || None || 32,228 || 48–41 |- style="background:#bfb" | 90 || July 18 || @ Devil Rays || 3–2 || Curt Schilling (14–4) || Albie Lopez (1–2) || None || 20,075 || 49–41 |- style="background:#bfb" | 91 || July 19 || @ Devil Rays || 16–3 || Chad Ogea (5–9) || Bryan Rekar (6–5) || None || 17,600 || 50–41 |- style="background:#fbb" | 92 || July 20 || @ Devil Rays || 4–5 (13) || Norm Charlton (1–2) || Steve Schrenk (0–1) || None || 30,868 || 50–42 |- style="background:#bfb" | 93 || July 21 || @ Brewers || 7–0 || Robert Person (4–4) || Scott Karl (7–8) || Jim Poole (1) || 21,933 || 51–42 |- style="background:#fbb" | 94 || July 22 || @ Brewers || 0–5 || Hideo Nomo (9–2) || Randy Wolf (5–1) || None || 29,777 || 51–43 |- style="background:#bfb" | 95 || July 23 (1) || Braves || 6–5 || Amaury Telemaco (2–0) || Rudy Seánez (5–1) || Wayne Gomes (14) || see 2nd game || 52–43 |- style="background:#fbb" | 96 || July 23 (2)