|| 29–27 || L2 |- style="text-align:center; background-color:#bbb" | — || May 30 || Yankees || colspan=8|Postponed (rain). Makeup date August 3. |- style="text-align:center; background-color:#fbb" | 57 || May 31 || @ Yankees || 1–4 || Happ (5–3) || Sale (1–7) || Chapman (16) || Yankee Stadium || 45,556 || 29–28 || L3 |- |- style="text-align:center; background-color:#fbb" | 58 || Jun 1 || @ Yankees || 3–5 || Green (1–2) || Porcello (4–5) || Chapman (17) || Yankee Stadium || 46,307 || 29–29 || L4 |- style="text-align:center; background-color:#bfb" | 59 || Jun 2 || @ Yankees || 8–5 || Price (3–2) || Sabathia (3–2) || Workman (2) || Yankee Stadium || 40,068 || 30–29 || W1 |- style="text-align:center; background-color:#bfb" | 60 || Jun 4 || @ Royals || 8–3 || Rodríguez (6–3) || Barlow (1–2) || — || Kauffman Stadium || 13,184 || 31–29 || W2 |- style="text-align:center; background-color:#bfb" | 61 || Jun 5 || @ Royals || 8–0 || Sale (2–7) || Junis (4–6) || — || Kauffman Stadium || 15,523 || 32–29 || W3 |- style="text-align:center; background-color:#bfb" | 62 || Jun 6 || @ Royals || 7–5 || Brewer (1–2) || Duffy (3–3) || Barnes (4) || Kauffman Stadium || 19,928 || 33–29 || W4 |- style="text-align:center; background-color:#fbb" | 63 || Jun 7 || Rays || 1–5 || Chirinos (7–2) || Porcello (4–6) || — || Fenway Park || 36,803 || 33–30 || L1 |- style="text-align:center; background-color:#fbb" | 64 || Jun 8 (1) || Rays || 2–9 || Yarbrough (5–2) || Smith (0–2) || — || Fenway Park || 35,564 || 33–31 || L2 |- style="text-align:center; background-color:#bfb" | 65 || Jun 8 (2) || Rays || 5–1 || Price (4–2) || Poche (0–1) || — || Fenway Park || 37,048 || 34–31 || W1 |- style="text-align:center; background-color:#fbb" | 66 || Jun 9 || Rays || 1–6 || Snell (4–5) || Rodríguez (6–4) || — || Fenway Park || 34,643 || 34–32 || L1 |- style="text-align:center; background-color:#fbb" | 67 || Jun 10 || Rangers || 3–4 (11) || Chavez (2–1) || Brasier (2–3) || Martin (2) || Fenway Park || 34,422 || 34–33 || L2 |- style="text-align:center; background-color:#fbb" | 68 || Jun 11 || Rangers || 5–9 || Jurado (4–2) || Hernández (0–1) || — || Fenway Park || 35,121 || 34–34 || L3 |- style="text-align:center; background-color:#bfb" | 69 || Jun 12 || Rangers || 4–3 || Barnes (3–1) ||