| Team: | Saskatchewan Roughriders |
| Year: | 1999 |
| Record: | 3–15 |
| Division Place: | 4th, West |
| Coach: | Cal Murphy |
| General Manager: | Alan Ford |
| Stadium: | Taylor Field |
| Playoffs: | did not qualify |
| Mop: | Mike Saunders |
| Moc: | Colin Scrivener |
| Mor: | Neal Smith |
| Uniform: | Image:CFL SSK Jersey 1995.png --> |
| Shortnavlink: | Roughriders seasons |
The 1999 Saskatchewan Roughriders finished in fourth place in the West Division with a 3–15 record and missed the playoffs. It was their worst record for a season in the current 18-game schedule and their worst since going 2–14 in the 1980 season.
| Round | Pick | Player | Position | School/Club Team |
|---|---|---|---|---|
| 2 | 10 | Indianapolis | ||
| 3 | 18 | Idaho State | ||
| 4 | 26 | Guelph | ||
| 5 | 33 | York | ||
| 6 | 41 | Alberta | ||
| Week | Date | Opponent | Score | Result | Attendance |
|---|---|---|---|---|---|
| A | Wed, June 23 | at Edmonton Eskimos | 27–3 | Loss | 35,313 |
| B | Tues, June 29 | vs. Calgary Stampeders | 34–24 | Loss | 18,591 |
| BC Lions | 18 | 13 | 5 | 0 | 429 | 373 | 26 | Details | |
| Calgary Stampeders | 18 | 12 | 6 | 0 | 503 | 393 | 24 | Details | |
| Edmonton Eskimos | 18 | 6 | 12 | 0 | 459 | 502 | 12 | Details | |
| 18 | 3 | 15 | 0 | 370 | 592 | 6 | Details |
| Week | Date | Opponent | Score | Result | Attendance | Record | |
|---|---|---|---|---|---|---|---|
| 1 | Wed, July 7 | at Calgary Stampeders | L 18–28 | 0–1 | 31,878 | ||
| 2 | Fri, July 16 | at Edmonton Eskimos | L 6–39 | 0–2 | 32,113 | ||
| 3 | Fri, July 23 | vs. BC Lions | L 21–32 | 0–3 | 19,785 | ||
| 4 | Fri, July 30 | vs. Toronto Argonauts | W 20–15 | 1–3 | 18,256 | ||
| 5 | Thur, Aug 5 | at Hamilton Tiger-Cats | L 17–63 | 1–4 | 16,423 | ||
| 6 | Fri, Aug 13 | vs. Calgary Stampeders | L 22–37 | 1–5 | 19,545 | ||
| 7 | Fri, Aug 20 | vs. Edmonton Eskimos | W 29–27 | 2–5 | 16,554 | ||
| 8 | Thur, Aug 26 | at BC Lions | L 21–28 | 2–6 | 21,617 | ||
| 9 | Sun, Sept 5 | vs. Winnipeg Blue Bombers | W 42–17 | 3–6 | 29,249 | ||
| 10 | Sat, Sept 11 | at Toronto Argonauts | L 3–28 | 3–7 | 17,216 | ||
| 11 | Fri, Sept 17 | vs. Edmonton Eskimos | L 38–41 | 3–8 | 18,231 | ||
| 12 | Fri, Sept 24 | at Winnipeg Blue Bombers | L 18–24 | 3–9 | 18,727 | ||
| 13 | Sun, Oct 3 | vs. Montreal Alouettes | L 26–41 | 3–10 | 17,715 | ||
| 14 | Mon, Oct 11 | at Montreal Alouettes | L 7–43 | 3–11 | 19,461 | ||
| 15 | Sun, Oct 17 | vs. Calgary Stampeders | L 31–34 | 3–12 | 16,448 | ||
| 16 | Sun, Oct 24 | vs. Hamilton Tiger-Cats | L 12–42 | 3–13 | 18,166 | ||
| 17 | Sat, Oct 30 | at Edmonton Eskimos | L 21–34 | 3–14 | 33,850 | ||
| 18 | Fri, Nov 5 | at BC Lions | L 18–19 | 3–15 | 19,378 |