| Managers | Tommy Bryce, (Sacked March 1999) John Lambie, (Appointed March 1999) |
| Final League Position | 8th in 2nd Division |
| Club Directory | |
| Team Group | |
| Squad List |
| July | 18 | Stranraer | Friendly | 3-2 | Johnston (2), Morgan | 500 | ||
| July | 20 | Stenhousemuir | Friendly | 2-1 | Dunn, Morgan | 250 | ||
| July | 25 | LE HARVE | Friendly | 0-3 | – | 1,421 | ||
| July | 27 | WALSALL | Friendly | 1-1 | Morgan | 712 | ||
| Aug | 1 | East Fife | League Cup 1st Round | 2-3 | Lauchlan, Morgan | 1,000 | After extra-time | |
| Aug | 4 | INVERNESS CALEDONIAN THISTLE | (Bell's 2nd Division) | 0-1 | – | 1,905 | ||
| Aug | 15 | Forfar Athletic | (Bell's 2nd Division) | 1-0 | Lauchlan | 1,053 | ||
| Aug | 22 | QUEEN OF THE SOUTH | (Bell's 2nd Division) | 2-2 | Morgan, Dunn | 1,963 | ||
| Aug | 29 | Clyde | (Bell's 2nd Division) | 2-1 | Morgan (2) | 2,621 | ||
| Sep | 5 | ALLOA ATHLETIC | (Bell's 2nd Division) | 1-0 | Morgan | 1,655 | ||
| Sep | 12 | STIRLING ALBION | (Bell's 2nd Division) | 1-0 | Bryce | 2,000 | ||
| Sep | 19 | East Fife | (Bell's 2nd Division) | 3-1 | Dunn (2), Lauchlan | 1,314 | ||
| Sep | 26 | ARBROATH | (Bell's 2nd Division) | 2-0 | Bryce, Morgan | 2,006 | ||
| Oct | 3 | Livingston | (Bell's 2nd Division) | 0-1 | – | 5,200 | ||
| Oct | 11 | FORFAR ATHLETIC | (Bell's 2nd Division) | 2-0 | Morgan, Bryce | 2,870 | ||
| Oct | 17 | Inverness Caledonian Thistle | (Bell's 2nd Division) | 2-3 | McDonald, Archibald | 2,598 | ||
| Oct | 24 | CLYDE | (Bell's 2nd Division) | 0-2 | – | 2,627 | ||
| Oct | 31 | Alloa Athletic | (Bell's 2nd Division) | 1-3 | Flannigan | 1,469 | ||
| Nov | 7 | EAST FIFE | (Bell's 2nd Division) | 0-1 | – | 1,870 | ||
| Nov | 14 | Stirling Albion | (Bell's 2nd Division) | 0-2 | – | 1,513 | ||
| Nov | 21 | Arbroath | (Bell's 2nd Division) | 0-1 | – | 1,121 | ||
| Nov | 28 | LIVINGSTON | (Bell's 2nd Division) | 1-3 | Dunn | 2,341 | ||
| Dec | 5 | Arbroath | (Tennent's) Scottish Cup 1st Round | 2-1 | Tosh, Dunn | 1,333 | ||
| Dec | 12 | Queen of the South | (Bell's 2nd Division) | 0-0 | – | 1,731 | ||
| Dec | 19 | INVERNESS CALEDONIAN THISTLE | (Bell's 2nd Division) | 2-1 | Tosh, Connell | 2,141 | ||
| Dec | 26 | Clyde | (Bell's 2nd Division) | 1-0 | McDonald | 2,673 | ||
| Jan | 2 | COWDENBEATH | (Tennent's) Scottish Cup 2nd Round | 5-2 | Tosh (4), Dunn | 3,019 | ||
| Jan | 13 | ALLOA ATHLETIC | (Bell's 2nd Division) | 2-1 | Dunn, O.g. | 1,502 | Rescheduled from (Sat) 9th January | |
| Jan | 16 | Arbroath | (Bell's 2nd Division) | 0-0 | – | 2,105 | ||
| Jan | 23 | DUNFERMLINE ATHLETIC | (Tennent's) Scottish Cup 3rd Round | 1-2 | Dunn | 4,650 | ||
| Jan | 30 | Livingston | (Bell's 2nd Division) | 1-1 | Dunn | 3,293 | ||
| Feb | 6 | East Fife | (Bell's 2nd Division) | 0-1 | – | 1,241 | ||
| Feb | 17 | STIRLING ALBION | (Bell's 2nd Division) | 0-1 | – | 1,203 | ||
| Feb | 20 | QUEEN OF THE SOUTH | (Bell's 2nd Division) | 1-3 | Dunn | 1,510 | ||
| Feb | 27 | Forfar Athletic | (Bell's 2nd Division) | 1-2 | Jamieson | 662 | ||
| Mar | 6 | Arbroath | (Bell's 2nd Division) | 1-0 | Lauchlan | 1,000 | ||
| Mar | 13 | CLYDE | (Bell's 2nd Division) | 0-1 | – | 3,341 | ||
| Mar | 20 | LIVINGSTON | (Bell's 2nd Division) | 1-1 | Dunn | 2,112 | ||
| Mar | 25 | MOTHERWELL | Friendly | 0-1 | – | 665 | ||
| Apr | 3 | Arbroath | (Bell's 2nd Division) | 1-2 | Dunn | 1,301 | ||
| Apr | 10 | EAST FIFE | (Bell's 2nd Division) | 2-2 | Houston, Audiu | 1,811 | ||
| Apr | 17 | Stirling Albion | (Bell's 2nd Division) | 0-3 | – | 1,664 | ||
| Apr | 24 | Inverness Caledonian Thistle | (Bell's 2nd Division) | 2-3 | Dunn, Jamieson | 3,246 | ||
| May | 1 | FORFAR ATHELTIC | (Bell's 2nd Division) | 1-0 | McDonald | 2,539 | ||
| May | 8 | Queen of the South | (Bell's 2nd Division) | 2-2 | Lauchlan (2) | 2,335 | ||
| Others: | ||||||||
| July | 14 | Ayr United | Closed Door Friendly | 4-1 | Morgan, Dunn (3) | 100 | Played at Saracen Park, Ashfield Juniors | |
| July | 16 | Clydebank | Closed Door Friendly | 1-0 | W Callaghan | 150 | Played at Saracen Park, Ashfield Juniors | |
| ? | ? | Hamilton Academical | Closed Door Friendly | 2-5 | McHarg, Johnston | |||
| July | 21 | Queen's Park | Friendly | 0-1 | – | 130 | ||
| Aug | 7 | Albion Rovers | Friendly | 2-2 | Martin, Bryce | 150 | ||
| Aug | 19 | MORTON | Reserve League West | 0-2 | – | |||
| Aug | ? | Hamilton Academical | Reserve League West | 2-2 | Dunn (2) | |||
| Sep | 3 | CLYDE | Reserve League Cup 1st Round | 3-2 | Dunn, Donaghy, McKenzie | |||
| Sept | 8 | Clyde | Reserve League West | 2-1 | Callaghan W, Dunn | |||
| Sep | 15 | STRANRAER | Reserve League West | 2-1 | Callaghan W (2) | |||
| Sep | 22 | St Mirren | Reserve League West | 2-4 | Martin, Johnston | |||
| Oct | 8 | STRANRAER | Reserve League Cup Quarter-Final | 6-3 | Callaghan W (2), McKenzie (2), Houston, McArthur | |||
| Oct | ? | QUEEN'S PARK | Reserve League West | 1-2 | McKenzie | |||
| Oct | 13 | Airdrieonians | Reserve League West | 1-3 | Johnston | |||
| Oct | 29 | Motherwell | Closed Door Friendly | 1-1 | ? | Played at Clelend Park, Motherwell | ||
| Nov | 2 | Morton | Reserve League West | 1-2 | Morgan | |||
| Nov | 9 | HAMILTON ACADEMICAL | Reserve League West | 1-1 | Dunn | |||
| Nov | 13 | St Mirren | SFA Youth Cup 2nd Round | 2-2 | ? | |||
| Nov | 18 | Albion Rovers | Reserve League West | 5-0 | Dunn (3), Dair (2) | |||
| Nov | 24 | CLYDE | Reserve League West | 1-0 | Houston | |||
| Dec | ? | Stranraer | Reserve League West | 1-4 | O.g. | |||
| Dec | ? | ST MIRREN | Reserve League West | 3-0 | Johnston (3) | |||
| Dec | 27 | Shettleston Juniors | Closed Door Friendly | 6-1 | Bryce (3), Lauchlan, Houston, Johnston | |||
| Jan | 27 | Queen's Park | Reserve League West | 3-1 | McCann, Lauchlan, Johnston, | |||
| Feb | 2 | AIRDRIEONIANS | Reserve League West | 1-1 | Frame | |||
| Mar | 29 | Scottish Junior Select | Friendly | 1-2 | D Trialist | 200 | Played at Linithgow Rose | |
| Apr | 12 | LIVINGSTON | Reserve League Cup Semi-Final | 1-2 | Frame | |||
| Apr | 20 | AYR UNITED | Reserve League West | 3-4 | McCann, McKenzie, Reid | |||
| Apr | ? | Alloa Athletic | Reserve League West | 5-2 | McKenzie, Fisher, Trialist (3) | |||
| May | 4 | ALBION ROVERS | Reserve League West | 0-0 | – | |||
| May | ? | ? | Reserve League West | ? | ? | |||
| May | ? | ? | Reserve League West | ? | ? | |||