| 2019-08-19 19:45:15August 19, 2019 | Cambridge City U18  | 3 - 4 |  St Ives Town U18 | 19:45:1519:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-09-02 19:45:44September 2, 2019 | St Ives Town U18 | 2 - 4 |  March Town United U18 | 19:45:4419:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-09-12 19:45:43September 12, 2019 | Deeping Rangers U18  | 1 - 1 | St Ives Town U18 | 19:45:4319:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-09-16 19:45:49September 16, 2019 | St Ives Town U18 | 4 - 2 |  Biggleswade Town U18 | 19:45:4919:45 | The FA Youth Cup | N/A | Match Report |
| 2019-09-23 19:45:43September 23, 2019 | St Ives Town U18 | 2 - 1 |  Godmanchester Rovers U18 | 19:45:4319:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-09-30 19:45:19September 30, 2019 | St Ives Town U18 | 0 - 3 |  AFC Dunstable U18 | 19:45:1919:45 | The FA Youth Cup | N/A | Match Report |
| 2019-10-07 19:45:31October 7, 2019 | St Ives Town U18 | 2 - 0 |  Wisbech St Mary U18 | 19:45:3119:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-10-17 19:45:26October 17, 2019 | Holbeach United U18  | 2 - 1 | St Ives Town U18 | 19:45:2619:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-11-20 19:45:05November 20, 2019 | St Ives Town U18 | 4 - 0 | Holbeach United U18 | 19:45:0519:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2019-12-04 19:45:17December 4, 2019 | Godmanchester Rovers U18 | 1 - 1 | St Ives Town U18 | 19:45:1719:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2020-01-22 19:45:14January 22, 2020 | St Ives Town U18 | 2 - 3 |  Peterborough Sports U18 | 19:45:1419:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2020-01-25 11:00:23January 25, 2020 | Park Farm Pumas U18 Black  | 1 - 4 | St Ives Town U18 | 11:00:2311:00 | Hunts County U18 Cup | N/A | Match Report |
| 2020-01-28 19:45:20January 28, 2020 | Wisbech St Mary U18 | 0 - 2 | St Ives Town U18 | 19:45:2019:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2020-02-05 19:45:39February 5, 2020 | St Ives Town U18 | 1 - 0 | Deeping Rangers U18 | 19:45:3919:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2020-03-04 19:45:44March 4, 2020 | St Ives Town U18 | 1 - 1 | Cambridge City U18 | 19:45:4419:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |
| 2020-03-11 19:45:46March 11, 2020 | St Neots Town U18  | 2 - 1 | St Ives Town U18 | 19:45:4619:45 | Thurlow Nunn Youth League West Division | N/A | Match Report |