| 2026-07-21 19:45:00July 21, 2026 | Clyde | - | Annan Athletic | 19:45:007:45 pm | League Cup | N/A |
| 2026-04-25 15:00:00April 25, 2026 | Clyde | 3 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2026-01-31 15:00:00January 31, 2026 | Annan Athletic | 1 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2025-11-22 15:00:00November 22, 2025 | Clyde | 1 - 0 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2025-10-25 15:00:40October 25, 2025 | Clyde | 2 - 3 | Annan Athletic | 15:00:403:00 pm | Scottish Cup | N/A |
| 2025-09-13 15:00:00September 13, 2025 | Annan Athletic | 0 - 6 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2023-05-19 19:35:54May 19, 2023 | Clyde | 1 - 2 | Annan Athletic | 19:35:547:35 pm | Scottish League One | N/A |
| 2023-05-16 19:35:44May 16, 2023 | Annan Athletic | 3 - 1 | Clyde | 19:35:447:35 pm | Scottish League One | N/A |
| 2019-05-18 15:00:00May 18, 2019 | Clyde | 2 - 0 | Annan Athletic | 15:00:003:00 pm | Scottish League One | N/A |
| 2019-05-14 19:45:00May 14, 2019 | Annan Athletic | 1 - 0 | Clyde | 19:45:007:45 pm | Scottish League One | N/A |
| 2019-03-23 15:00:00March 23, 2019 | Clyde | 2 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2019-02-09 15:00:00February 9, 2019 | Annan Athletic | 1 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2018-12-15 15:00:00December 15, 2018 | Clyde | 1 - 0 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2018-09-01 15:00:00September 1, 2018 | Annan Athletic | 1 - 2 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2018-03-17 15:00:00March 17, 2018 | Annan Athletic | 1 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2018-01-02 15:00:00January 2, 2018 | Clyde | 0 - 0 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2017-11-25 15:00:00November 25, 2017 | Annan Athletic | 0 - 0 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2017-08-12 15:00:00August 12, 2017 | Clyde | 2 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2017-07-15 15:00:00July 15, 2017 | Clyde | 2 - 1 | Annan Athletic | 15:00:003:00 pm | League Cup | N/A |
| 2017-04-08 15:00:00April 8, 2017 | Clyde | 2 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2017-02-25 15:00:00February 25, 2017 | Annan Athletic | 1 - 0 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2016-12-31 15:00:00December 31, 2016 | Clyde | 2 - 3 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2016-08-20 15:00:00August 20, 2016 | Annan Athletic | 3 - 2 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2016-03-22 19:45:00March 22, 2016 | Clyde | 2 - 1 | Annan Athletic | 19:45:007:45 pm | Scottish League Two | N/A |
| 2016-03-05 15:00:00March 5, 2016 | Annan Athletic | 3 - 3 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2015-12-26 15:00:00December 26, 2015 | Annan Athletic | 2 - 3 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2015-09-12 15:00:00September 12, 2015 | Clyde | 4 - 2 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2015-03-28 15:00:00March 28, 2015 | Annan Athletic | 0 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2015-03-03 19:45:00March 3, 2015 | Clyde | 1 - 0 | Annan Athletic | 19:45:007:45 pm | Scottish League Two | N/A |
| 2014-12-27 15:00:00December 27, 2014 | Annan Athletic | 2 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2014-09-27 15:00:00September 27, 2014 | Clyde | 1 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2014-04-05 15:00:00April 5, 2014 | Clyde | 0 - 3 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2014-01-18 15:00:00January 18, 2014 | Annan Athletic | 0 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2013-12-03 19:45:00December 3, 2013 | Clyde | 2 - 1 | Annan Athletic | 19:45:007:45 pm | Scottish League Two | N/A |
| 2013-09-21 15:00:00September 21, 2013 | Annan Athletic | 1 - 2 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2013-03-16 15:00:00March 16, 2013 | Annan Athletic | 0 - 1 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2013-01-05 15:00:00January 5, 2013 | Clyde | 2 - 3 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2012-11-24 15:00:00November 24, 2012 | Annan Athletic | 1 - 3 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2012-09-01 15:00:00September 1, 2012 | Clyde | 2 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2012-03-17 15:00:00March 17, 2012 | Clyde | 1 - 1 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2012-01-07 15:00:00January 7, 2012 | Annan Athletic | 1 - 0 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2011-11-12 15:00:00November 12, 2011 | Clyde | 0 - 0 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2011-08-27 15:00:00August 27, 2011 | Annan Athletic | 1 - 0 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2011-04-02 15:00:00April 2, 2011 | Annan Athletic | 1 - 0 | Clyde | 15:00:003:00 pm | Scottish League Two | N/A |
| 2011-03-29 19:30:00March 29, 2011 | Annan Athletic | 0 - 2 | Clyde | 19:30:007:30 pm | Scottish League Two | N/A |
| 2011-02-05 15:00:00February 5, 2011 | Clyde | 0 - 2 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2010-09-18 15:00:00September 18, 2010 | Clyde | 0 - 2 | Annan Athletic | 15:00:003:00 pm | Scottish League Two | N/A |
| 2008-07-26 15:00:00July 26, 2008 | Clyde | 2 - 0 | Annan Athletic | 15:00:003:00 pm | Challenge Cup | N/A |
