| Barclay Shield | 7 | 13 Dec 08, 20 Dec 08 | Plenty 150 DL Connelley 29* M Johnson 26 AJ Amalfi 26 D Love 25 | def | Lalor Stars 9/147 A Volpe 36 MT Abeyratne 36 P Hubber 4/52 D Love 2/23 | Plenty Park |
| Barclay Reserve | 7 | 13 Dec 08, 20 Dec 08 | Lalor Stars 143 J Vasilev 31 M Johnson 3/14 D Smith 2/15 W Barclay 2/36 RP Hoysted 2/39 | tied | Plenty 143 S Keane 32 SR Jones 3/12 J Bugden 2/10 JW Scott 2/50 | W.A. Smith Reserve #1 |
| C Grade | 7 | 13 Dec 08, 20 Dec 08 | Plenty 103 LJ Smith 27 C Wills 7/31 | def by | Bundoora 3/112 J Flint 53* JX Nicholas 28 A Carnell 2/60 | Diamond Hills Reserve |
| D Grade | 7 | 20 Dec 08 | Research 9/148 S Weston 31 J Anderson 30 SJ Crump 3/11 J McMahon 2/7 | def by | Plenty 7/218(cc) J Baines 98* R Abbatangelo 34 SJ Crump 34 S Scales 3/28 | Kangaroo Ground Oval |
| G Grade | 6 | 13 Dec 08, 20 Dec 08 | Mill Park 4/169 B Jones 101* A Grixti 32 | def | Plenty 9/151(cc) JR Byrne 29 A Barclay 28 J Brown 26 M Soligo 4/25 A Dass 2/14 | Findon Reserve |
| U16 (1) Teal | 6 | 13 Dec 08, 20 Dec 08 | Plenty 5/102 J Kett 50* N Gaylor 2/21 | def | Riverside 9/99(cc) L Brophy-Hassett 28 A Cotter 3/12 D Cocking 3/16 T Fothergill 2/25 | Plenty Park |
| U16 (2) | 2 | 18 Oct 08, 25 Oct 08 | Plenty
| def by | Montmorency-Lower Plenty
| Diamond Hills Reserve |
| U14 (1) Blue | 6 | 13 Dec 08, 20 Dec 08 | Riverside 2/111(cc) N Karam 43* | def | Plenty 5/90(cc) J Bergman 2/7 | Whatmough Park #1 |
| U14 (2) Teal | 2 | 18 Oct 08, 25 Oct 08 | Lower Plenty
| def | Plenty
| Anthony Beale Reserve West |
| U12 (1) Blue | 6 | 12 Dec 08, 19 Dec 08 | Research 6/101(cc) T Grindal 27* A Bonnici 2/5 | def | Plenty 6/93(cc) L Banthorpe 29* | Research Park |
| U12 (2) Teal | 6 | 12 Dec 08, 19 Dec 08 | Plenty 7/70(cc) J Hogan 4/8 | def | North Eltham Wanderers White 8/67(cc) J Castles 26* J Sacchetta 3/1 M Harris 2/7 J Gavin 2/8 | Diamond Hills Reserve |
| U12 Modified | 11 | 19 Dec 08 | Plenty Blue
| v | South Morang Black
| Plenty Park |
| U12 Modified | 11 | 19 Dec 08 | Thomastown United
| v | Plenty Gold
| Thomastown East Reserve #2 |