| Date | Competition | Home Team | Score | Score | Away Team | Report | Pictures | Notes |
| JAN | | | | | | | | |
| 2 | League Division 1 | Rangers | 4 | 1 | Celtic | Report | Pictures | |
| 03 | Glasgow League | Celtic | 2 | 1 | Clyde | Report | Pictures | |
| 7 | League Division 1 | Celtic | 4 | 1 | Dundee | Report | Pictures | |
| 14 | Scottish Cup | 6th G.R.V | 1 | 8 | Celtic | Report | Pictures | |
| 21 | Glasgow League | Celtic | 2 | 2 | Queen’s Park | Report | Pictures | |
| FEB | | | | | | | | |
| 4 | Scottish Cup | Celtic | 3 | 0 | St Bernard’s | Report | Pictures | |
| 11 | Glasgow League | Clyde | 2 | 5 | Celtic | Report | Pictures | |
| 18 | Scottish Cup | Celtic | A | A | Queen’s Park | Report | Pictures | Match abandoned due to lack of light |
| 25 | Scottish Cup | Celtic | 2 | 1 | Queen’s Park | Report | Pictures | |
| MAR | | | | | | | | |
| 11 | Scottish Cup | Celtic | 4 | 2 | Port Glasgow Athletic | Report | Pictures | |
| 18 | Glasgow League | Third Lanark | 2 | 3 | Celtic | Report | Pictures | |
| 25 | Friendly | Blackburn Rovers | 3 | 1 | Celtic | Report | Pictures | |
| APR | | | | | | | | |
| 01 | Friendly | Dundee | 2 | 2 | Celtic | Report | Pictures | |
| 03 | Friendly | Hibernian | 1 | 1 | Celtic | Report | Pictures | |
| 03 | Glasgow League | Celtic | 2 | 1 | Third Lanark | Report | Pictures | |
| 10 | Friendly | Celtic | 0 | 2 | Wigan County | Report | Pictures | |
| 14 | Friendly | Dumfries Hibs | 0 | 10 | Celtic | Report | Pictures | |
| 15 | Friendly | Celtic | 2 | 0 | Liverpool | Report | Pictures | |
| 17 | Friendly | Johnstone | 0 | 5 | Celtic | Report | Pictures | |
| 22 | Scottish Cup | Celtic | 2 | 0 | Rangers | Report | Pictures | Scottish Cup Final, Celtic win for second time |
| 25 | Friendly | Abercorn | 3 | 3 | Celtic | Report | Pictures | |
| 26 | Glasgow League | Celtic | 3 | 0 | Partick Thistle | Report | Pictures | |
| 29 | Glasgow League | Partick Thistle | 1 | 3 | Celtic | Report | Pictures | |
| MAY | | | | | | | | |
| 1 | Friendly | Aberdeen | 1 | 5 | Celtic | Report | | |
| 2 | Friendly | Fair City Athletic | 1 | 10 | Celtic | Report | | |
| 3 | Friendly | Stevenston Thistle | 2 | 4 | Celtic | Report | | |
| 6 | Glasgow League | Celtic | 4 | 1 | Rangers | Report | Pictures | |
| 8 | Friendly | West Calder | 2 | 2 | Celtic | Report | Pictures | |
| 10 | Glasgow League | Queen’s Park | 1 | 5 | Celtic | Report | Pictures | |
| 11 | Friendly | Port Glasgow Athletic | 3 | 3 | Celtic | Report | Pictures | |
| 13 | Glasgow League | Rangers | 1 | 1 | Celtic | Report | Pictures | |
| 15 | Friendly | Royal Albert | 0 | 1 | Celtic | Report | | |
| 20 | Glasgow Charity Cup | Celtic | 4 | 0 | Queen’s Park | Report | Pictures | |
| 27 | Glasgow Charity Cup | Celtic | 2 | 0 | Rangers | Report | | |
| | Season Review | | | | | | |
| | Statistics 1898-99 | | | | | | |
| | | | | | | | |
| | | | | | | | |
| | League Table 1898-99 | | | | | | |
| | Scottish Cup, Fixtures & Results 1898-99 | | | | | | |
| | | | | | | | |
| | | | | | | | |
| | Celtic Team Line-Up 1899-1900 | | | | | | |
| | | | | | | | | |
| AUG | | | | | | | | |
| 19 | League Division 1 | Celtic | 3 | 2 | Clyde | Report | Pictures | |
| 26 | League Division 1 | Kilmarnock | 2 | 2 | Celtic | Report | Pictures | Opening of Rugby Park |
| 28 | Friendly | Celtic | 2 | 2 | Rangers | Report | Pictures | Sandy McMahon Testimonial |
| SEP | | | | | | | | |
| 2 | League Division 1 | Celtic | 5 | 2 | Third Lanark | Report | Pictures | |
| 9 | League Division 1 | Celtic | 2 | 1 | Hibernian | Report | Pictures | |
| 16 | Glasgow Cup 1st Rd | Celtic | 5 | 1 | Partick Thistle | Report | Pictures | |
| 18 | League Division 1 | Hibernian | 1 | 1 | Celtic | Report | Pictures | |
| 21 | Friendly | Celtic | 2 | 0 | The Kaffirs | Report | Pictures | South African side; The first black tourist team to play in the UK, Basuto XI |
| 23 | League Division 1 | Clyde | 0 | 5 | Celtic | Report | Pictures | |
| 25 | League Division 1 | Third Lanark | 0 | 3 | Celtic | Report | Pictures | |
| 30 | League Division 1 | Celtic | 0 | 2 | Heart of Midlothian | Report | Pictures | |
| OCT | | | | | | | | |
| 7 | League Division 1 | Rangers | 3 | 3 | Celtic | Report | Pictures | |
| 14 | Glasgow Cup SF | Linthouse | 1 | 5 | Celtic | Report | Pictures | At Govandale Park. Att – 5,000. |
| 21 | League Division 1 | St Mirren | 2 | 2 | Celtic | Report | Pictures | |
| 28 | League Division 1 | Celtic | 5 | 0 | St Bernard’s | Report | Pictures | Opening of the Grand Stand later named the Grant Stand. |
| NOV | | | | | | | | |
| 4 | League Division 1 | Heart of Midlothian | 3 | 2 | Celtic | Report | Pictures | |
| 11 | Glasgow Cup Final | Rangers | 1 | 1 | Celtic | Report | pictures | At Cathkin Park. Att – 10,000. |
| 18 | Glasgow Cup Final Replay | Rangers | 1 | 0 | Celtic | Report | Pictures | At Cathkin Park. Att – 8,000. |
| 25 | League Division 1 | Dundee | 1 | 2 | Celtic | Report | Pictures | |
| DEC | | | | | | | | |
| 2 | League Division 1 | St Bernard’s | 1 | 1 | Celtic | Report | Pictures | |
| 9 | League Division 1 | Celtic | 3 | 1 | St Mirren | Report | Pictures | |
| 16 | League Division 1 | Celtic | 3 | 3 | Kilmarnock | Report | Pictures | |
| 23 | League Division 1 | Celtic | 1 | 1 | Dundee | Report | Pictures | |
| 25 | Friendly | Blackburn Rovers | 3 | 2 | Celtic | Report | Pictures | |
| 29 | Inter-City League | Hibernian | 1 | 0 | Celtic | Report | Pictures | |
| | | | | | | | | |