| 233: 1999 Trade for Nathan Eagleton and Brett Montgomery | |||
| Port Adelaide | Montgomery (126 games) + #28 (Guerra - 255 games) | expected 112 |
actual 381 |
| Western Bulldogs | Eagleton (221 games) | expected 77 |
actual 221 |
| 235: 1999 Trade for Jason Ball | |||
| Sydney | Ball (90 games) | expected 43 |
actual 90 |
| West Coast | #11 (Glass - 270 games) + #41 (Munro - 18 games) | expected 116 |
actual 288 |
| 236: 1999 Trade for Brendon Fewster | |||
| Fremantle | Fewster (37 games) | expected 85 |
actual 37 |
| West Coast | #16 (Haynes - 65 games) | expected 70 |
actual 65 |
| 237: 1999 Trade for Stephen O'Reilly | |||
| Carlton | O'Reilly (12 games) | expected 43 |
actual 12 |
| Fremantle | #16 (Haynes - 65 games) + #46 (Butler - 0 games) | expected 88 |
actual 65 |
| 238: 1999 Trade for Troy Longmuir | |||
| Fremantle | Longmuir (55 games) | expected 77 |
actual 55 |
| Melbourne | #19 (Green - 254 games) + #63 (O'Brien - 0 games) | expected 74 |
actual 254 |
| 239: 1999 Trade for Stefan Carey | |||
| Brisbane | Carey (3 games) | expected 74 |
actual 3 |
| Sydney | #21 (Stevens - 144 games) | expected 57 |
actual 144 |
| 240: 1999 Trade for Michael Mansfield | |||
| Carlton | Mansfield (54 games) | expected 23 |
actual 54 |
| Geelong | #31 (Chapman - 280 games) | expected 44 |
actual 280 |
| 241: 1999 Trade for David Calthorpe | |||
| Brisbane | #32 (Giansiracusa - 265 games) | expected 44 |
actual 265 |
| North Melbourne | Calthorpe (13 games) | expected 23 |
actual 13 |
| 242: 1999 Trade for Troy Cook | |||
| Fremantle | Cook (150 games) | expected 74 |
actual 150 |
| Sydney | #34 (Davis - 225 games) | expected 42 |
actual 225 |
| 243: 1999 Trade for Stephen Powell | |||
| Melbourne | Powell (44 games) | expected 37 |
actual 44 |
| Western Bulldogs | #35 (Wiggins - 12 games) | expected 40 |
actual 12 |
| 244: 1999 Trade for Leon Cameron | |||
| Richmond | Cameron (84 games) | expected 39 |
actual 84 |
| Western Bulldogs | #37 (Hahn - 181 games) + #66 (Hargrave - 203 games) | expected 50 |
actual 384 |
| 245: 1999 Trade for Justin Plapp | |||
| Richmond | #39 (Homewood - 0 games) | expected 33 |
actual 0 |
| St Kilda | Plapp (26 games) | expected 28 |
actual 26 |
| 246: 1999 Trade for Matthew Bishop | |||
| Melbourne | #42 (Clark - 1 games) | expected 21 |
actual 1 |
| Port Adelaide | Bishop (132 games) | expected 47 |
actual 132 |
| 247: 1999 Trade for Matthew Clarke | |||
| Adelaide | Clarke (118 games) | expected 43 |
actual 118 |
| Brisbane | #6 (Cupido - 53 games) + #21 (Stevens - 144 games) | expected 182 |
actual 197 |
| 248: 1999 Trade for Scott Welsh | |||
| Adelaide | Welsh (129 games) + #67 (Shirley - 151 games) | expected 90 |
actual 280 |
| North Melbourne | #77 (Smith - 4 games) | expected 5 |
actual 4 |
| 249: 1999 Trade for Lance Picioane | |||
| Adelaide | #79 (Singh - 0 games) | expected 4 |
actual 0 |
| Hawthorn | Picioane (58 games) | expected 76 |
actual 58 |
| 250: 1999 Trade for Mark Kinnear and Andrew Schauble | |||
| Collingwood | Kinnear (0 games) + #34 (Davis - 225 games) | expected 193 |
actual 225 |
| Sydney | Schauble (88 games) | expected 28 |
actual 88 |
| 251: 1999 Trade for Leigh Colbert and Cameron Mooney | |||
| Geelong | Mooney (210 games) + #15 (Spriggs - 69 games) + #17 (Bray - 0 games) + #47 (Enright - 332 games) | expected 172 |
actual 611 |
| North Melbourne | Colbert (104 games) + #53 (Lasscock - 0 games) + #67 (Shirley - 151 games) | expected 66 |
actual 255 |
| 252: 1999 Trade for Clinton King and Steven McKee | |||
| Collingwood | McKee (64 games) + #7 (Roach - 1 games) | expected 145 |
actual 65 |
| Richmond | King (58 games) + #3 (Fiora - 140 games) | expected 247 |
actual 198 |
| 255: 1999 Trade for Trent Bartlett and Michael Martin | |||
| Brisbane | Martin (10 games) | expected 74 |
actual 10 |
| Western Bulldogs | Bartlett (42 games) + #32 (Giansiracusa - 265 games) | expected 106 |
actual 307 |
| 512: 1999 Trade for Jonathon Robran and Andrew Ukovic | |||
| Collingwood | Ukovic (17 games) | expected 54 |
actual 17 |
| Essendon | Robran (8 games) + #40 (Hille - 197 games) | expected 73 |
actual 205 |
| Hawthorn | #33 (Clarke - 96 games) + #48 (Bateman - 177 games) | expected 60 |
actual 273 |