| 2019-09-08 12:00:37September 8, 2019 | Biggleswade Town U14  | 0 - 4 |  St Ives Town U14 | 12:00:3712:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-09-15 11:00:39September 15, 2019 | St Ives Town U14 | 0 - 3 |  Needham Market U14 | 11:00:3911:00 | U14 Challenge Cup | N/A |
| 2019-09-22 10:30:40September 22, 2019 | Godmanchester Town U14  | 2*(5) - 2 (4) | St Ives Town U14 | 10:30:4010:30 | Hunts U14's Cup | N/A |
| 2019-10-06 11:00:41October 6, 2019 | St Ives Town U14 | 1 - 0 |  Bury Town U14 | 11:00:4111:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-10-13 11:00:28October 13, 2019 | St Ives Town U14 | 2 - 1 |  Stotfold U14 | 11:00:2811:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-10-20 10:30:59October 20, 2019 | Godmanchester Town U14 | 1 - 0 | St Ives Town U14 | 10:30:5910:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-11-03 10:30:56November 3, 2019 | Saffron Walden Community Youth U14  | 0 - 4 | St Ives Town U14 | 10:30:5610:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-11-24 10:30:23November 24, 2019 | Berkhamsted Youth U14  | 3 - 2 | St Ives Town U14 | 10:30:2310:30 | U14 Treasurers Cup | N/A |
| 2019-12-01 13:30:40December 1, 2019 | St Ives Town U14 | 6 - 2 | Saffron Walden Community Youth U14 | 13:30:4013:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2019-12-15 14:00:57December 15, 2019 | Soham Town Rangers Youth U14  | 4 - 0 | St Ives Town U14 | 14:00:5714:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-01-05 10:30:52January 5, 2020 | Stotfold U14 | 1 - 4 | St Ives Town U14 | 10:30:5210:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-01-12 11:30:42January 12, 2020 | Bury Town U14 | 3 - 6 | St Ives Town U14 | 11:30:4211:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-01-26 11:00:51January 26, 2020 | Bedford Town (Youth Development) U14  | 5 - 1 | St Ives Town U14 | 11:00:5111:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-02-02 11:00:18February 2, 2020 | Hitchin Town Youth U14  | 2 - 1 | St Ives Town U14 | 11:00:1811:00 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-02-23 10:30:10February 23, 2020 | St Ives Town U14 | 0 - 1 | Hitchin Town Youth U14 | 10:30:1010:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-03-01 10:30:01March 1, 2020 | St Ives Town U14 | 3 - 1 | Biggleswade Town U14 | 10:30:0110:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |
| 2020-03-08 10:30:48March 8, 2020 | St Ives Town U14 | 0 - 3 | Godmanchester Town U14 | 10:30:4810:30 | Eastern Junior Alliance U14 Yellow (Cambs) | N/A |