1999 Cleveland Indians season Game log May

| Date_ | Opponent | Score | Loss | Attendance | Record |
|---|---|---|---|---|---|
| May 11 | Orioles | 11 - 6 | Ponson (2-3) | 40587 | 23-9 |
| May 12 | Orioles | 6 - 5 | Timlin (1-2) | 42939 | 24-9 |
| May 14 | @ Tigers | 4 - 2 | Brocail (1-1) | 21844 | 25-9 |
| May 15 | @ Tigers | 12 - 7 | Mlicki (1-3) | 39769 | 26-9 |
| May 16 | @ Tigers | 9 - 3 | Wright (4-1) | 29731 | 26-10 |
| May 17 | @ White Sox | 13 - 9 | Navarro (2-4) | 17101 | 27-10 |
| May 18 | @ White Sox | 13 - 0 | Baldwin (2-4) | 13429 | 28-10 |
| May 19 | @ White Sox | 13 - 7 | Parque (5-3) | 14854 | 29-10 |
| May 21 | Tigers | 9 - 6 | Shuey (2-2) | 43290 | 29-11 |
| May 22 | Tigers | 6 - 2 | Wright (4-2) | 40991 | 29-12 |