1999 Toronto Blue Jays season Game log May

| Date_ | Opponent | Score | Loss | Attendance | Record |
|---|---|---|---|---|---|
| May 21 | @ Red Sox | 5 - 2 | Escobar (3-2) | 27284 | 21-23 |
| May 22 | @ Red Sox | 6 - 4 | Carpenter (3-4) | 32038 | 21-24 |
| May 23 | @ Red Sox | 10 - 8 | Hentgen (4-2) | 28559 | 21-25 |
| May 24 | @ Tigers | 12 - 6 | Moehler (4-4) | 13038 | 22-25 |
| May 25 | @ Tigers | 5 - 3 | Mlicki (1-5) | 13087 | 23-25 |
| May 26 | @ Tigers | 9 - 5 | Blair (1-5) | 14177 | 24-25 |
| May 28 | Yankees | 10 - 6 | Carpenter (3-5) | 30355 | 24-26 |
| May 29 | Yankees | 8 - 3 | Hentgen (4-3) | 40175 | 24-27 |
| May 30 | Yankees | 8 - 3 | Wells (5-5) | 39111 | 24-28 |