Park || 37,032 || 23–20 || W1 |- style="text-align:center; background-color:#fbb" | 44 || May 17 || Astros || 1–3 || Harris (1–0) || Porcello (3–4) || Osuna (11) || Fenway Park || 35,558 || 23–21 || L1 |- style="text-align:center; background-color:#fbb" | 45 || May 18 || Astros || 3–7 || James (1–0) || Velázquez (1–3) || || Fenway Park || 36,887 || 23–22 || L2 |- style="text-align:center; background-color:#bfb" | 46 || May 19 || Astros || 4–3 || Walden (6–0) || Valdez (1–2) || Workman (1) || Fenway Park || 35,796 || 24–22 || W1 |- style="text-align:center; background-color:#bfb" | 47 || May 20 || @ Blue Jays || 12–2 || Price (2–2) || Jackson (0–1) || — || Rogers Centre || 26,794 || 25–22 || W2 |- style="text-align:center; background-color:#fbb" | 48 || May 21 || @ Blue Jays || 3–10 || Stroman (2–6) || Rodríguez (4–3) || — || Rogers Centre || 14,407 || 25–23 || L1 |- style="text-align:center; background-color:#bfb" | 49 || May 22 || @ Blue Jays || 6–5 (13) || Hembree (1–0) || Cordero (0–1) || — || Rogers Centre || 18,285 || 26–23 || W1 |- style="text-align:center; background-color:#bfb" | 50 || May 23 || @ Blue Jays || 8–2 || Weber (1–0) || Gaviglio (3–1) || — || Rogers Centre || 36,526 || 27–23 || W2 |- style="text-align:center; background-color:#fbb" | 51 || May 24 || @ Astros || 3–4 || Miley (5–2) || Sale (1–6) || Osuna (13) || Minute Maid Park || 35,606 || 27–24 || L1 |- style="text-align:center; background-color:#fbb" | 52 || May 25 || @ Astros || 3–4 || Osuna (3–0) || Barnes (2–1) || — || Minute Maid Park || 40,722 || 27–25 || L2 |- style="text-align:center; background-color:#bfb" | 53 || May 26 || @ Astros || 4–1 || Rodríguez (5–3) || Verlander (8–2) || Walden (1) || Minute Maid Park || 41,502 || 28–25 || W1 |- style="text-align:center; background-color:#bfb" | 54 || May 27 || Indians || 12–5 || Porcello (4–4) || Rodríguez (1–5) || — || Fenway Park || 37,113 || 29–25 || W2 |- style="text-align:center; background-color:#fbb" | 55 || May 28 || Indians || 5–7 || Wittgren (2–0) || Lakins (0–1) || Hand (14) || Fenway Park || 32,984 || 29–26 || L1 |- style="text-align:center; background-color:#fbb" | 56 || May 29 || Indians || 9–14 || Bieber (4–2) || Weber (1–1) || Hand (15) || Fenway Park || 34,824