Shelbourne FC Fixtures 1999-2000
FAI National League
| DATE | OPPOSITION | Venue |
| 15/8/99 | Galway United | Tolka Park |
| 22/8/99 | Bohemians | Dalymount Park |
| 5/9/99 | UCD | Tolka Park |
| 12/9/99 | Finn Harps | Balleybofey |
| 19/9/99 | Cork City | Tolka Park |
| 26/9/99 | St.Patrick's Athletic | Inchicore |
| 3/10/99 | Sligo Rovers | The Showgrounds, Sligo |
| 10/10/99 | Drogheda United | Tolka Park |
| 17/10/99 | Waterford United | Waterford |
| 24/10/99 | Derry City | Tolka Park |
| 31/10/99 | Shamrock Rovers | Santry Stadium |
| 7/11/99 | Galway United | Terryland Park, Galway |
| 14/11/99 | Bohemians | Tolka Park |
| 21/11/99 | UCD | UCD Campus |
| 28/11/99 | Finn Harps | Tolka Park |
| 5/12/99 | Cork City | Turners Cross, Cork |
| 12/12/99 | St.Patrick's Athletic | Tolka Park |
| 19/12/999 | Sligo Rovers | Tolka Park |
| 26/12/99 | Drogheda United | United Park, Drogheda |
| 2/1/00 | Waterford United | Tolka Park |
| 16/1/00 | Derry City | The Brandywell, Derry |
| 23/1/00 | Shamrock Rovers | Tolka Park |
| 30/1/00 | Galway United | Tolka Park |
| 13/2/00 | Bohemians | Dalymount Park |
| 20/2/00 | UCD | Tolka Park |
| 27/2/00 | Finn Harps | Ballybofey |
| 12/3/00 | Cork City | Tolka Park |
| 19/3/00 | St.Patrick's Athletic | Inchicore |
| 26/3/00 | Sligo Rovers | The Showgrounds, Sligo |
| 2/3/00 | Drogheda United | Tolka Park |
| 9/3/00 | Waterford United | Waterford |
| 16/3/00 | Derry City | Tolka Park |
| 23/3/00 | Shamrock Rovers | Santry Stadium |
FAI Cup
| Date | Round |
| 9/1/00 | 1st |
| 6/2/00 | 2nd |
| 5/3/00 | Quarter Finals |
| 2/4/00 | Semi-Finals |
| 30/4/00 | Final |
FAI League Cup
| Date | Opposition | Venue |
| 29/8/99 | Home Farm | To be decided |
| 8/9/99 | 2nd Round | |
| 6/10/99 | Quarter Final | |
| 1/12/99 | Semi Final | |
| to be decided | Final |