1999 Edmonton Eskimos
Don Matthews is named the head coach of the Green and Gold. Edmonton would finish third in the West with a record of 6-12 and lose in the West Semifinal to the Calgary Stampeders. In his first year in Edmonton, receiver Terry Vaughn had 11 touchdowns and 1, 057 yards receiving, while quarterback Nealon Greene threw for 2,046 yards. Running back Troy Mills carried the ball for a team-best 1,022 yards.
| 1999 (51st season) |
| Record: 6-12 (3rd West) |
| Home: 2-7 | Away: 4-5 |
| Playoffs: 0-1 | Lost Division Semifinal |
| Head coach: Don Matthews (1st season) |
| CFL All-Stars: Leo Groenewegen |
| West All-Stars: Leo Groenewegen, Doug Petersen, Terry Ray, Val St. Germain, Terry Vaughn |
| Hall of Fame: |
| Major award winners: |
| Wall of Honour: |
| Date | Opponent | Result (record) |
| July 9 | vs British Columbia Lions | L 25–13 (0-1) |
| July 16 | vs Saskatchewan Roughriders | W 39–6 (1-1) |
| July 22 | at Calgary Stampeders | L 41–27 (1-2) |
| July 29 | at Hamilton Tiger-Cats | L 54–8 (1-3) |
| August 6 | vs Montreal Alouettes | L 20–13 (1-4) |
| August 13 | at Winnipeg Blue Bombers | W 56–26 (2-4) |
| August 20 | at Saskatchewan Roughriders | L 29–27 (2-5) |
| August 27 | vs Hamilton Tiger-Cats | L 30–23 (2-6) |
| September 6 | at Calgary Stampeders | W 33–30 (3-6) |
| September 10 | vs Calgary Stampeders | L 38–13 (3-7) |
| September 17 | at Saskatchewan Roughriders | W 41–38 (4-7) |
| September 26 | vs Toronto Argonauts | L 20–16 (4-8) |
| October 3 | vs Winnipeg Blue Bombers | L 27–19 (4-9) |
| October 11 | at British Columbia Lions | W 26–20 (5-9) |
| October 17 | vs British Columbia Lions | L 21–13 (5-10) |
| October 23 | at Montreal Alouettes | L 36–33 (5-11) |
| October 30 | vs Saskatchewan Roughriders | W 34–21 (6-11) |
| November 6 | at Toronto Argonauts | L 20–15 (6-12) |
| November 11 | at Calgary Stampeders | L 17-30 Division Semifinal |