1999 Cleveland Indians season Game log May

| Date_ | Opponent | Score | Loss | Attendance | Record |
|---|---|---|---|---|---|
| May 23 | Tigers | 7 - 4 | Jones (0-1) | 40874 | 30-12 |
| May 24 | White Sox | 10 - 3 | Gooden (2-1) | 43208 | 30-13 |
| May 25 | White Sox | 3 - 1 | Parque (5-4) | 42161 | 31-13 |
| May 26 | White Sox | 6 - 2 | Sirotka (2-6) | 43228 | 32-13 |
| May 28 | Red Sox | 12 - 5 | Wright (4-3) | 43287 | 32-14 |
| May 29 | Red Sox | 4 - 2 | Colón (6-2) | 43255 | 32-15 |
| May 30 | Red Sox | 4 - 2 | Gooden (2-2) | 43207 | 32-16 |
| May 31 | @ Yankees | 7 - 1 | Hernandez (5-5) | 46605 | 33-16 |