1999 Ansett Australia Cup Round of 16 Round of 16

| Home_team | Home_team_score | Away_team | Away_team_score | Ground | Crowd | Date_ | Time_ |
|---|---|---|---|---|---|---|---|
| Fremantle | 7.8 (50) | Hawthorn | 14.12 (96) | Subiaco Oval | 12088 | Thursday 11 February 1999 | 6:00 PM |
| Brisbane Lions | 12.15 (87) | Carlton | 4.4 (28) | The Gabba | 16318 | Friday, 12 February 1999 | 7:00 PM |
| Sydney | 12.13 (85) | Collingwood | 11.8 (74) | Manuka Oval | 13313 | Saturday, 13 February 1999 | 5:00 PM |
| Essendon | 14.8 (92) | Western Bulldogs | 18.12 (120) | Marrara Oval | 14211 | Saturday, 13 February 1999 | 6:00 PM |
| Richmond | 8.15 (63) | West Coast | 6.10 (46) | Waverley Park | 11325 | Thursday, 18 February 1999 | 8:00 PM |
| Adelaide | 8.9 (57) | Port Adelaide | 13.15 (93) | Football Park | 40577 | Friday 19 February 1999 | 8:00 PM |
| Geelong | 9.7 (61) | Kangaroos | 20.14 (134) | Waverley Park | 13514 | Saturday, 20 February 1999 | 8:00 PM |