| 19/08/1899 | KILMARNOCK | D1 | H | 6,000 | 0-1 | L | |
| 26/08/1899 | Third Lanark | D1 | A | 4,000 | 1-5 | L | STEEL |
| 02/09/1899 | ST.BERNARDS | D1 | H | 3,000 | 4-3 | W | BRUCE, STEEL, YOUNG, McDONALD |
| 09/09/1899 | DUNDEE | D1 | H | 4,000 | 4-0 | W | ORR, HASTINGS, YOUNG 2 |
| 16/09/1899 | Hearts | D1 | A | 5,500 | 0-3 | L | |
| 23/09/1899 | Hibernian | D1 | A | 2,500 | 1-5 | L | WYLIE |
| 30/09/1899 | CLYDE | D1 | H | 2,000 | 3-0 | W | STEEL 2, YOUNG |
| 07/10/1899 | HIBERNIAN | D1 | H | 5,000 | 1-1 | D | CAIRNEY |
| 14/10/1899 | Dundee | D1 | A | 7,000 | 2-5 | L | YOUNG, ORR (P) |
| 21/10/1899 | CELTIC | D1 | H | 7,000 | 2-2 | D | McNEILLY (P), GRAY |
| 28/10/1899 | CLYDE | WLG | H | | 1-3 | L | GRAY |
| 04/11/1899 | THIRD LANARK | D1 | H | 3,000 | 1-1 | D | WYLIE |
| 11/11/1899 | Kilmarnock | D1 | A | 2,000 | 2-2 | D | STEEL, WYLIE |
| 18/11/1899 | HEARTS | D1 | H | 3,000 | 2-2 | D | WYLIE, RENNIE OG |
| 25/11/1899 | Clyde | D1 | A | | 1-3 | L | WYLIE |
| 02/12/1899 | RANGERS | D1 | H | 4,000 | 1-3 | L | WYLIE |
| 09/12/1899 | Celtic | D1 | A | 4,000 | 1-3 | L | STEEL |
| 16/12/1899 | Rangers | D1 | A | | 1-4 | L | YOUNG |
| 23/12/1899 | Partick This | WLG | A | | 1-4 | L | McNEILLY (P) |
| 30/12/1899 | St.Bernards | D1 | A | | 3-3 | D | ORR 2, YOUNG |
| 06/01/1900 | PARTICK THIS | WLG | H | | 4-3 | W | LINDSAY, STEEL, CHEYNE, YOUNG |
| 13/01/1900 | Hearts | SC1 | A | 3,000 | 0-0 | D | |
| 20/01/1900 | HEARTS | SC1R | H | | 0-3 | L | |
| 03/02/1900 | Morton | WLG | A | | 0-1 | L | |
| 10/03/1900 | KILMARNOCK | WLG | H | | 2-1 | W | LINDSAY (2) |
| 17/03/1900 | JOHNSTONE | RC2 | H | | 1-2 | L | STEEL |
| 24/03/1900 | Port Glasgow | WLG | A | | 2-4 | L | WYLIE, ORR |
| 07/04/1900 | St. Bernard’s* | P/0 | N | | 2-1 | W | WYLIE, ORR |
| 14/04/1900 | Clyde | WLG | A | 1,000 | 5-0 | W | STEEL (2), WYLIE, LINDSAY, ORR |
| 21/04/1900 | Kilmarnock | WLG | A | | 1-1 | D | LINDSAY |
| 01/05/1900 | MORTON | WLG | H | | 2-1 | W | |
| 12/05/1900 | PORT GLASGOW | WLG | H | | 5-1 | W | STEEL, ORR, YOUNG, WYLIE, LINDSAY |