|| Lowe (3-2) || Betancourt (2) || 16,070 || 12-13 |-align="center" bgcolor="#ffbbbb" | 26 || May 5 || Red Sox || 9 – 5 || Arroyo (1-1) || D'Amico (1-2) || || 17,370 || 12-14 |-align="center" bgcolor="#ffbbbb" | 27 || May 6 || Red Sox || 5 – 2 || Martínez (4-2) || Sabathia (1-1) || Foulke (6) || 26,825 || 12-15 |-align="center" bgcolor="#ffbbbb" | 28 || May 7 || @ Orioles || 3 – 2 (10) || Julio (1-0) || Durbin (2-3) || || 34,324 || 12-16 |-align="center" bgcolor="#ffbbbb" | 29 || May 8 || @ Orioles || 10 – 7 || Parrish (3-1) || Stewart (0-2) || Julio (4) || 30,687 || 12-17 |-align="center" bgcolor="#ffbbbb" | 30 || May 9 || @ Orioles || 12 – 11 || López (3-1) || Riske (0-1) || Julio (5) || 35,778 || 12-18 |-align="center" bgcolor="#bbffbb" | 31 || May 10 || @ Red Sox || 10 – 6 || Durbin (3-3) || Kim (1-1) || ||35,257 || 13-18 |-align="center" bgcolor="#ffbbbb" | 32 || May 11 || @ Red Sox || 5 – 3 || Embree (1-0) || Jiménez (0-2) || Foulke (7) || 35,401 || 13-19 |-align="center" bgcolor="#bbffbb" | 33 || May 12 || @ Red Sox || 6 – 4 || Lee (4-0) || Wakefield (2-2) || || 35,371 || 14-19 |-align="center" bgcolor="#bbffbb" | 34 || May 14 || Devil Rays || 8 – 7 (10) || White (1-0) || Carter (1-2) || || 19,796 || 15-19 |-align="center" bgcolor="#bbffbb" | 35 || May 15 || Devil Rays || 9 – 7 || Westbrook (3-1) || Zambrano (3-4) || || 18,040 || 16-19 |-align="center" bgcolor="#bbffbb" | 36 || May 16 || Devil Rays || 10 – 0 || Sabathia (2-1) || Waechter (1-4) || || 19,499 || 17-19 |-align="center" bgcolor="#bbffbb" | 37 || May 17 || White Sox || 7 – 2 || Lee (5-0) || Díaz (0-1) || || 15,617 || 18-19 |-align="center" bgcolor="#ffbbbb" | 38 || May 18 || White Sox || 4 – 2 || Garland (3-2) || Durbin (3-4) || Koch (7) || 15,298 || 18-20 |-align="center" bgcolor="#ffbbbb" | 39 || May 19 || White Sox || 15 – 3 || Schoeneweis (4-1) || Davis (1-3) || || 17,205 || 18-21 |-align="center" bgcolor="#ffbbbb" | 40 || May 21 || @ Devil Rays || 5 – 3 || Miller (1-1) || Sabathia (2-2) || Báez (6) || 10,213