In the Canberra League in 1999 there were six Clubs, Ainslie, Belconnen, Eastlake, Queanbeyan, Tuggeranong and Weston Creek Wildcats.
Former Melbourne, Carlton and Port Power AFL player Brent Heaver was appointed coach.
Ainslie finished out of the finals for the second consecutive year.
Aldo Dipetta played his 100th First Grade game for the Club.
Brian Stanislaus was the Club’s leading goal kicker with 30 goals.
ACT Representative players were: Paul Gambale, Dion Grant, Brent Heaver and Chris Smith.
- Captain/Coach: Brent Heaver
- Managers: John Rebecca, Brian Dobson
1999-Ainslie Second Grade
The Second Grade finished the home and away games on top of the ladder.
In the Second Semi-Final Ainslie defeated Belconnen by 9 points to go through to the Grand Final.
- Final score: Ainslie 12.10-82 def Belconnen 11.7-73
- Goal kickers for Ainslie: J Read 5, P Crosby 2, T Klep 2, M Sheridan 2, M Sinclair 1
In the Grand Final Ainslie again met Belconnen and defeated them by 31 points to win the Premiership.
- Final score: Ainslie 14.14-98 def Belconnen 9.13-67
- Goal kickers for Ainslie: J Read 4, P Crosby 2, B Rebecca 2, M Sheridan 2, J Burgess 1,T Klep 1, E Smith 1, M Sinclair 1
The Ainslie Second Grade Premiership Team was:
- Backs: Sean Woodland, Simeon Blowse, Ryan Storey
- Half Backs: Paul Colussi, Ben Battisson, Paul Salter
- Centres: Evan Smith, Andrew Wainwright, Try Klep
- Half Forwards: Jason Burgess, Mark Sinclair, Brent Rebecca
- Forwards: Dean McGee, John Read, Peter Crosby
- Rucks: Andrew Kouvaras, Aaron Tyndall, Marcus Sheridan
- Interchange: Jesse Brooks, Chris Tournier, Sam Truesdale
Andrew Kouvaras was awarded the medal for the Best Player in the Second Grade Grand Final.
John Read led the League’s goal kicking in Second Grade with 65 goals.
- Coach: Wayne Kelty
- Captains: Jason Burgess and Sean Woodland
- Manager: Tom Munyard
Canberra District Division
The District team played in the finals but were defeated by Gungahlin in the First Semi-Final to finish in fourth place.
- Coach: Dave Crawford
Women
The Ainslie Women’s team played off in the Semi-Final but were defeated to finish in fourth place.
- Coach: Jeff de Huis
Club Awards
First Grade
- Best & Fairest: Chris Smith
- Runner Up B&F: Paul Gambale
- Most Consistent: Todd Pulford
- Coach’s Award: Salem Kassem
Second Grade
- Best & Fairest: Andrew Kouvaras
- Runner Up B&F: Brent Rebecca
- Most Consistent: John Read
- Best in Finals: Andrew Kouvaras
District Division
- Best & Fairest: Steve Glowrey
- Runner Up B&F: Anthony Weston
- Most Consistent: Tim Chandler
- Leading Goalkicker: Graham Budd
- Most Improved: Ben Thornton
Women
- Best & fairest: Tracey Baxter
- Runner Up B&F: Christie Williams
- Leading Goalkicker: Jade McCormick
- Most Consistent: Anne Kirwan
- Most Improved: Tracey Axelby
Club Officials
- President: Garry Cox
- Secretary: Keith Heales
- Treasurer: Kel Duncan
- Senior Vice President: John Miller
- Vice President: Craig Smith
- Committee: Garry Cox, John Miller, Craig Smith, Keith Heales, Kel Duncan, Peter Ireland, Trevor Lond, Geoff McCormick, Stewart Morgan, Ian Muir, Peter Poke, Mark Sinclair
- Patron: Alan Ray