| Team: | Winnipeg Blue Bombers |
| Year: | 1999 |
| Record: | 6–12 |
| Division Place: | 4th, East |
| Coach: | Dave Ritchie |
| Stadium: | Winnipeg Stadium |
| Playoffs: | did not qualify |
| Uniform: | Image:CFL WPG Jersey 1998.png |
| Shortnavlink: | Blue Bombers seasons |
The 1999 Winnipeg Blue Bombers finished in fourth place in the East Division with a 6–12 record and failed to make the playoffs.
| Montreal Alouettes | 18 | 12 | 6 | 0 | 495 | 395 | 24 | |
| Hamilton Tiger-Cats | 18 | 11 | 7 | 0 | 603 | 378 | 22 | |
| Toronto Argonauts | 18 | 9 | 9 | 0 | 386 | 373 | 18 | |
| 18 | 6 | 12 | 0 | 362 | 601 | 12 |
| Week | Date | Opponent | Result | Record | |
|---|---|---|---|---|---|
| 1 | July 8 | vs. Hamilton Tiger-Cats | L 9–39 | 0–1 | |
| 2 | July 15 | vs. Toronto Argonauts | W 47–27 | 1–1 | |
| 3 | July 22 | at Montreal Alouettes | L 18–30 | 1–2 | |
| 4 | July 29 | at BC Lions | W 30–18 | 2–2 | |
| 5 | Aug 6 | at Toronto Argonauts | L 7–40 | 2–3 | |
| 6 | Aug 13 | vs. Edmonton Eskimos | L 26–56 | 2–4 | |
| 7 | Aug 19 | at Calgary Stampeders | L 17–29 | 2–5 | |
| 8 | Aug 26 | vs. Calgary Stampeders | L 11–36 | 2–6 | |
| 9 | Sept 5 | at Saskatchewan Roughriders | L 17–42 | 2–7 | |
| 10 | Sept 12 | vs. BC Lions | L 16–20 | 2–8 | |
| 11 | Sept 18 | at Hamilton Tiger-Cats | L 15–65 | 2–9 | |
| 12 | Sept 24 | vs. Saskatchewan Roughriders | W 24–18 | 3–9 | |
| 13 | Oct 3 | at Edmonton Eskimos | W 27–19 | 4–9 | |
| 14 | Oct 10 | vs. Hamilton Tiger-Cats | L 16–43 | 4–10 | |
| 15 | Oct 17 | vs. Montreal Alouettes | W 32–29 | 5–10 | |
| 16 | Oct 22 | at Toronto Argonauts | L 23–32 | 5–11 | |
| 17 | Oct 29 | vs. Toronto Argonauts | W 18–13 | 6–11 | |
| 18 | Nov 7 | at Montreal Alouettes | L 10–45 | 6–12 |