1999 Canadian Professional Soccer League season
| Season | 1999 |
|---|---|
| Champions | Toronto Olympians |
| Top goalscorer |  Eddy Berdusco (Toronto Olympians) |
← 1998 2000 → | |
The second Canadian Professional Soccer League season began on May 28, 1999 and concluded on October 2, 1999 with Toronto Olympians winning the Rogers Cup.
Changes from 1998 season
- Glen Shields changed name to Glen Shields Sun Devils
- The Oshawa Flames are added as an expansion team.
- The Mississauga Eagles P.S.C. folded after one season.
Final standings
Green indicates playoff berth clinched
| Place | Team | P | W | L | T | GF | GA | Points |
|---|---|---|---|---|---|---|---|---|
| 1 | Toronto Olympians | 14 | 13 | 0 | 1 | 56 | 7 | 40 |
| 2 | Toronto Croatia | 14 | 8 | 4 | 2 | 31 | 19 | 26 |
| 3 | Glen Shields Sun Devils | 14 | 7 | 4 | 3 | 34 | 18 | 24 |
| 4 | London City | 14 | 5 | 4 | 5 | 30 | 36 | 20 |
| 5 | Oshawa Flames | 14 | 3 | 6 | 5 | 19 | 26 | 14 |
| 6 | St. Catharines Wolves | 14 | 3 | 7 | 4 | 19 | 30 | 13 |
| 7 | York Region Shooters | 14 | 3 | 8 | 3 | 20 | 34 | 12 |
| 8 | North York Astros | 14 | 2 | 11 | 1 | 16 | 55 | 7 |
League Cup Finals
| Toronto Olympians | 3–0 | Toronto Croatia |
|---|---|---|
Handsor  40' Thomas 62' 66' |
Centennial Stadium: 450
Rogers Cup playoffs
Semifinals
| Toronto Croatia | 5–2 | Glen Shields Sun Devils |
|---|---|---|
| Jelic 6' J. Draganic 44' 72' (pk) Medeiros  60' Zajac 79' Mandekic 82' |
Vaglica 45+1' Delarovere 60' Glasgow 60' Hillman  75'  Powell 83' Antonucci 88' |
Civic Stadium: 100
| Toronto Olympians | 4–1 | London City |
|---|---|---|
| Kouzmanis 10' 73' (pk) 84' (pk) Capporella 33' |
Mesanovic 87' (pk) |
Civic Stadium: 100
Rogers Cup final
| Toronto Olympians | 2–0 | Toronto Croatia |
|---|---|---|
| Thomas 55' Handsor 75' |
Civic Stadium: 100
Individual awards
- CPSL MVP Award:: Elvis Thomas, Toronto Olympians
- CPSL Golden Boot: Eddie Berdusco, Toronto Olympians
- CPSL Goalkeeper of the Year Award: George Azcurra, Toronto Croatia
- CPSL Rookie of the Year Award: Semir Mesanovic, London City
- CPSL Coach of the Year Award: David Gee, Toronto Olympians; Tony LaFerrara, London City
- CPSL Referee of the Year Award: Silviu Petrescu
- CPSL Fair Play Award: Toronto Olympians
