Holbrook's Will Holmes' dazzling late season form was instrumental in the hard-working midfielder scoring a runaway victory in the Azzi medal on Monday night.
Holmes trailed Osborne's Connor Galvin who was the pre-count favourite by three votes with four rounds remaining.
But a late flurry of three best-on-ground performances in the final month of the season saw Holmes storm to 27 votes and score a shock win.
Surprisingly Galvin failed to poll a vote after round 12 and finished on 21.
Reigning medallist Matt Seiter grabbed third on 17.
Lockhart's Jordan Harrington didn't poll as well as expected to finish equal seventh with 13.
Holmes originally thought one of his team-mates was playing a practical joke when he received a call to inform him he had won the Azzi medal.
"It was very unexpected and there is so much talent in our league," Holmes said.
"When I got the call that I won, I thought it was a joke and one of my mate's was pulling my leg.
"But when I realised I had won, it has been slowly sinking in since I guess.
"I thought Jordy (Harrington) and Connor (Galvin) would have finished top-two for sure.
"I have no doubt their time will come in the near future."
Holmes credited a solid pre-season to his consistency and form this year and the faith shown in him by coach Matt Sharp.
"I put in the effort over the pre-season and talked to 'Sharpie' a lot about how to improve my consistency," he said.
"I really worked on that aspect where in previous seasons I was a bit off and on every week.
"So it was a focus of mine and I thought I did OK but it was but that was biggest difference now I guess.
"Sharpie showed a lot of faith in me and didn't try to hold me back and sort of gave me a licence to attack and get the ball.
"Each week I tried to do that and we are fortunate to have Sharpie as the club as coach."
Seiter was in second place after 10 rounds but a rib injury suffered in round 12 against Osborne robbed him of any chance of going back-to-back.
The dominant big man only played two more matches after suffering the injury.
Holmes was judged best-on-ground on six occasions and played the maximum possible of 15 matches.
He became only the third Brooker to win the award since they crossed from the Tallangatta league in 1999.
Big Brooker Noel Coutts won a hat-trick of medals from 2002-04.
Midfield maestro Mikal Bloom joined the honour roll in 2011.
Holmes has emerged through the junior ranks at Holbrook.
Brock-Burrum' Daniel Heagney edged out Culcairn's Jesse Kent to take out the reserves best and fairest award.
In a tight count only two votes separated the top-four.
Kent won a league medal in the fourths in 2005 and was president of Culcairn this season.
In the thirds, Lockhart's Noah Vennell clinched a thrilling two vote victory over Holbrook's Ben Parker.
The fourths was also a close count with Jindera's Bohdi Kerr edging out Howlong's Baxter Hamilton by three votes.
Osborne's Connor Galvin took out the WAW Player of the Year award.
Holbrook's Ewan Mackinlay was crowned the Rising Star.
Holbrook won the football club championship and Osborne the overall club championship trophy.
27: Will Holmes (Holbrook)
21: Connor Galvin (Osborne)
17: Matt Seiter (Brock-Burrum)
15: Jack Duck (RWW Giants)
14: Chris Duck (RWW Giants), 14: Jarrad Farwell (Henty)
13: Jordan Harrington (Lockhart), 13: Nathan Wardius (RWW Giants)
12: Ben Baker (Howlong), 12: Heath Ohlin (Henty), 12: Nicholas Madden (Osborne), 12: Tyson Neander (Brock-Burrum)
11: Ben Gould (Culcairn), 11: Daniel Middleton (Jindera), 11: Shannon Terlich (Henty)
10: Corey Smith (CDHBU), 10: Lachlan Trethowan (Holbrook), 10: Sam Livingstone (Osborne), 10: Samuel Scott (Henty)
15: Daniel Heagney (Brock-Burrum)
14: Jesse Kent (Culcairn)
13: Hamish Mackinlay (Holbrook), Jake Raves (Osborne)
12: Daniel Madden (Osborne)
11: Joshua Lewis (CDHBU), Matthew Tullberg (Lockhart)
10: Daniel Terlich (Henty)
33: Noah Vennell (Lockhart)
31: Ben Parker (Holbrook)
23: Harry Kreutzberger (RWW Giants)
21: Zachariah Mazzei (Howlong)
19: Joseph Muller (Culcairn)
17: Charlie Douglas (Osborne), Jack Kotzur (RWW Giants)
16: George Flanagan (Jindera), 16: Jayden Hucker (Holbrook), Logan Wright (Holbrook)
15: Blake Roulston (Henty)
33: Bodhi Kerr (Jindera)
30: Baxter Hamilton (Howlong)
26: Zac Klemke (Henty)
24: Edward Kreutzberger (RWW Giants), Max Tallent (Brock-Burrum)
21: Izak Schirmer (Holbrook)
19: Wil Jenkin (Holbrook)
17: Caleb Brown (Lockhart)
14: Jack Douglas (Osborne), Josh Williams (RWW Giants), Nicholas Boywer (Osborne), Oscar Preston (Holbrook)
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