south (1-0) vs fitzroy (1-0) lake oval
fitzroy beat south by 4 points to continue their title defence. fitzroy (2-0) travel to geelong. south (1-1) play essendon.
| South Melbourne | 0.3 2.5 3.6 5.8 | 38 | Sat 20-May-1899 3:00 PM Venue: Lake Oval |
| Fitzroy | 1.1 2.4 6.5 6.6 | 42 | Fitzroy won by 4 pts |
carlton (0-1) vs geelong (1-0) princess park
geelong beat carlton by 25 points. geelong (2-0) host fitzroy. carlton (0-2) host melbourne.
| Carlton | 0.1 0.2 1.4 1.5 | 11 | Sat 20-May-1899 3:00 PM Venue: Princes Park |
| Geelong | 2.0 3.3 3.4 5.6 | 36 | Geelong won by 25 pts |
st kilda (0-1) vs essendon (0-1) junction oval
essendon had 21 more shots in a 46 point win over st kilda. essendon (1-1) host south. st kilda (0-2) play collingwood.
| St Kilda | 1.1 1.1 2.2 3.2 | 20 | Sat 20-May-1899 3:00 PM Venue: Junction Oval |
| Essendon | 1.0 4.9 5.14 8.18 | 66 | Essendon won by 46 pts |
collingwood (0-1) vs melbourne (1-0) victoria park
melborune stun collingwood by 27 points. melbourne (2-0) play carton. collingwood (0-2) host st kilda.
| Collingwood | 0.2 1.2 2.2 4.3 | 27 | Sat 20-May-1899 3:00 PM Venue: Victoria Park |
| Melbourne | 2.4 3.7 6.8 7.12 | 54 | Melbourne won by 27 pts |
ladder
| Rd 2 Ladder | |||
| ME | 2 | 8 | 340.0 |
| GE | 2 | 8 | 236.8 |
| FI | 2 | 8 | 189.4 |
| SM | 2 | 4 | 185.0 |
| ES | 2 | 4 | 111.9 |
| CW | 2 | 0 | 50.0 |
| CA | 2 | 0 | 26.6 |
| SK | 2 | 0 | 23.6 |