The 1999 Winnipeg Blue Bombers finished in fourth place in the East Division with a 6–12 record and failed to make the playoffs.
| Round
|
Pick
|
Player
|
Position
|
School
|
|
|
| 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
|
[1]
Eastern All-Star Selections
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