| 1999 Playoffs |
| QUARTER FINALS |
| Quality Painting (8th) VS Sam Moran Club (1st) |
| Game 1: Sam Moran Club 7 Quality Painting 1 |
| Game 2: Sam Moran Club 11 Quality Painting 8 |
| Sam Moran Club wins series 2-0 |
| |
| Shamrock Pub (7th) VS Sidewalk Cafe (2nd) |
| Game 1: Sidewalk Cafe 5 Shamrock Pub 4 |
| Game 2: Sidewalk Cafe 21 Shamrock Pub 9 |
| Sidewalk Cafe wins series 2-0 |
| |
| L Street Tavern (6th) VS Murphy's Law (3rd) |
| Game 1: Murphy's Law 8 L Street Tavern 7 |
| Game 2: Murphy's Law 9 L Street Tavern 6 |
| Murphy's Law wins series 2-0 |
| |
| Seapoint Restaurant (5th) VS Quietman Pub (4th) |
| Game 1: Seapoint Restaurant 5 Quietman Pub 3 |
| Game 2: Seapoint Restaurant 11 Quietman Pub 5 |
| Seapoint Restaurant wins series 2-0 |
| |
| SEMI FINALS |
| Seapoint Restaurant (5th) VS Sam Moran Club (1st) |
| Game 1: Sam Moran Club 4 Seapoint Restaurant 3 |
| Game 2: Sam Moran Club 5 Seapoint Restaurant 2 |
| Game 3: Sam Moran Club 15 Seapoint Restaurant 12 |
| Sam Moran Club wins series 3-0 |
| |
| Murphy's Law (3rd) VS Sidewalk Cafe (2nd) |
| Game 1: Sidewalk Cafe 8 Murphy's Law 4 |
| Game 2: Murphy's Law 7 Sidewalk Cafe 3 |
| Game 3: Sidewalk Cafe 4 Murphy's Law 0 |
| Game 4: Sidewalk Cafe 11 Murphy's Law 3 |
| Sidewalk Cafe wins series 3-1 |
| |
| FINALS |
| Sidewalk Cafe (2nd) VS Sam Moran Club (1st) |
| Game 1: Sam Moran Club 7 - Sidewalk Cafe 3 |
| Game 2: Sam Moran Club 5 - Sidewalk Cafe 1 |
| Game 3: Sidewalk Cafe 11 - Sam Moran Club 3 |
| Game 4: Sam Moran Club 8 - Sidewalk Cafe 6 |
| Game 5: Sam Moran Club 7 - Sidewalk Cafe 5 |
| Sam Moran Club wins series 4-1 |
