Morrow (1–2) || || 11,785 || 18–18 |- bgcolor="bbffbb" | 37 || May 10 || @ Twins || W 10–2 || Porcello (3–2) || Liriano (2–5) || || 38,949 || 19–18 |- bgcolor="bbffbb" | 38 || May 11 || @ Twins || W 9–7 || Benoit (1–2) || Capps (1–2) || Valverde (8) || 38,938|| 20–18 |- bgcolor="bbffbb" | 39 || May 13 || Royals || W 3–1 || Verlander (4–3) || Hochevar (3–4) || Valverde (9) || 33,641 || 21–18 |- bgcolor="bbffbb" | 40 || May 14 || Royals || W 3–0 || Penny (4–3) || Francis (0–5) || Valverde (10) || 37,647 || 22–18 |- bgcolor="bbbbbb" | – || May 15 || Royals || colspan=6 | Postponed (rain) – rescheduled for September 1. |- bgcolor="ffbbbb" | 41 || May 16 || Blue Jays || L 4–2 || Drabek (3–2) || Benoit (1–3) || Francisco (4)|| 20,444 || 22–19 |- bgcolor="bbbbbb" | – || May 17 || Blue Jays || colspan=6 | Postponed (rain) – rescheduled for June 27. |- bgcolor="ffbbbb" | 42 || May 18 || @ Red Sox || L 1–0 || Bard (1–3) || Schlereth (0–1) || Papelbon (8)|| 37,311|| 22–20 |- bgcolor="ffbbbb" | 43 || May 19 || @ Red Sox || L 4–3 || Papelbon (2–0) || Alburquerque (0–1) || || 37,660 || 22–21 |- bgcolor="ffbbbb" | 44 || May 20 || @ Pirates || L 10–1 || Karstens (3–2) || Penny (4–4) || || 24,396 || 22–22 |- bgcolor="ffbbbb" | 45 || May 21 || @ Pirates || L 6–2 || Correia (6–4) || Scherzer (6–1) || Hanrahan (13) || 37,958 || 22–23 |- bgcolor="bbffbb" | 46 || May 22 || @ Pirates || W 2–0 || Porcello (4–2) || Maholm (1–7) || Valverde (11) || 25,124 || 23–23 |- bgcolor="bbffbb" | 47 || May 23 || Rays || W 6–3 || Furbush (1–0) || Hellickson (5–3) || || 21,550 || 24–23 |- bgcolor="bbffbb" | 48 || May 24 || Rays || W 7–6 || Alburquerque (1–1) || Ramos (0–1) || Benoit (1) || 24,133 || 25–23 |- bgcolor="bbbbbb" | – || May 25 || Rays || colspan=6 | Postponed (rain) – rescheduled for June 13. |- bgcolor="ffbbbb" | 49 || May 26 || Red Sox || L 14–1 (8) || Aceves (2–0) || Scherzer (6–2) || || 24,213 || 25–24 |- bgcolor="ffbbbb" | 50 || May 27 || Red Sox || L