1969 Chicago Cubs season Game log May

| Date_ | Opponent | Score | Loss | Attendance | Record |
|---|---|---|---|---|---|
| May 13 | Padres | 19 - 0 | Kelley (2-3) | 5080 | 22-11 |
| May 14 | Padres | 3 - 2 | Podres (3-3) | 9622 | 23-11 |
| May 16 | @ Astros | 11 - 0 | Dierker (5-4) | 17053 | 24-11 |
| May 17 | @ Astros | 5 - 4 | Nottebart (1-1) | 18307 | 24-12 |
| May 18 | @ Astros | 6 - 5 | Regan (5-1) | 13126 | 24-13 |
| May 20 | @ Dodgers | 7 - 0 | Sutton (4-4) | 21266 | 25-13 |
| May 21 | @ Dodgers | 3 - 1 | Hands (3-5) | 16688 | 25-14 |
| May 22 | @ Dodgers | 3 - 0 | Singer (5-4) | 17974 | 26-14 |
| May 23 | @ Padres | 6 - 0 | Ross (1-4) | 7936 | 27-14 |
| May 24 | @ Padres | 7 - 5 | Kelley (2-4) | 4432 | 28-14 |