148 || Sep 14 || @ Phillies || 2–1 || Barnes (5–4) || Neris (3–6) || Workman (13) || Citizens Bank Park || 40,688 || 78–70 || W2 |- style="text-align:center; background-color:#bfb" | 149 || Sep 15 || @ Phillies || 6–3 || Porcello (13–12) || Vargas (6–8) || Workman (14) || Citizens Bank Park || 39,061 || 79–70 || W3 |- style="text-align:center; background-color:#fbb" | 150 || Sep 17 || Giants || 6–7 || Rodríguez (6–9) || Kelley (0–2) || — || Fenway Park || 35,925 || 79–71 || L1 |- style="text-align:center; background-color:#fbb" | 151 || Sep 18 || Giants || 3–11 || Samardzija (11–12) || Chacín (3–11) || — || Fenway Park || 35,697 || 79–72 || L2 |- style="text-align:center; background-color:#bfb" | 152 || Sep 19 || Giants || 5–4 || Rodríguez (18–6) || Bumgarner (9–9) || Workman (15) || Fenway Park || 35,816 || 80–72 || W1 |- align="center" style="background: #993333; color: white" | 153 || Sep 20 || @ Rays || 4–5 || Castillo (4–8) || Kelley (0–3) || — || Tropicana Field || 17,117 || 80–73 || L1 |- style="text-align:center; background-color:#fbb" | 154 || Sep 21 || @ Rays || 4–5 || Castillo (5–8) || Smith (0–3) || — || Tropicana Field || 18,179 || 80–74 || L2 |- style="text-align:center; background-color:#bfb" | 155 || Sep 22 || @ Rays || 7–4 || Eovaldi (2–0) || Yarbrough (11–5) || — || Tropicana Field || 17,946 || 81–74 || W1 |- style="text-align:center; background-color:#fbb" | 156 || Sep 23 || @ Rays || 4–7 || Pruitt (3–0) || Poyner (0–1) || Poche (2) || Tropicana Field || 8,779 || 81–75 || L1 |- style="text-align:center; background-color:#bfb" | 157 || Sep 24 || @ Rangers || 12–10 || Rodríguez (19–6) || Jurado (7–11) || Workman (16) || Globe Life Park || 23,341 || 82–75 || W1 |- style="text-align:center; background-color:#bfb" | 158 || Sep 25 || @ Rangers || 10–3 || Porcello (14–12) || Allard (4–2) || — || Globe Life Park || 29,290 || 83–75 || W2 |- style="text-align:center; background-color:#fbb" | 159 || Sep 26 || @ Rangers || 5–7 || Minor (14–10) || Weber (2–4) || Leclerc (14) || Globe Life Park || 24,612 || 83–76 || L1 |- style="text-align:center; background-color:#fbb" | 160 || Sep 27 || Orioles || 1–4 || Wojciechowski (4–8) || Eovaldi (2–1) || — || Fenway Park || 34,533 || 83–77 || L2 |- style="text-align:center; background-color:#fbb" |