2006 Chicago Cubs season Game log May

| Date_ | Opponent | Score | Loss | Attendance | Record |
|---|---|---|---|---|---|
| May 1 | Pirates | 2–1 | Grabow (0–1) | 36602 | 14–10 |
| May 2 | Pirates | 8–0 | Guzmán (0–1) | 39110 | 14–11 |
| May 3 | @ Diamondbacks | 5–1 | Maddux (5–1) | 25335 | 14–12 |
| May 4 | @ Diamondbacks | 6–0 | Hill (0–1) | 24565 | 14–13 |
| May 5 | @ Padres | 1–0 | Williamson (2–2) | 37123 | 14–14 |
| May 6 | @ Padres | 2–1 | Howry (2–1) | 37745 | 14–15 |
| May 7 | @ Padres | 6–3 | Guzmán (0–2) | 39847 | 14–16 |
| May 8 | @ Padres | 8–3 | Maddux (5–2) | 24139 | 14–17 |
| May 9 | @ Giants | 6–1 | Hill (0–2) | 39357 | 14–18 |
| May 10 | @ Giants | 8–1 | Cain (1–5) | 39655 | 15–18 |
| May 11 | @ Giants | 9–3 | Marshall (2–1) | 38132 | 15–19 |