| 2018-09-16 10:30:48September 16, 2018 | AFC Sudbury U15  | 3 - 4 |  St Ives Town U15 | 10:30:4810:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-09-30 10:30:59September 30, 2018 | Haverhill Rovers U15  | 1 - 5 | St Ives Town U15 | 10:30:5910:30 | U15 Challenge Cup | 2018-19 | N/A |
| 2018-10-14 10:30:22October 14, 2018 | Warboys Colts U15  | 1 - 0 | St Ives Town U15 | 10:30:2210:30 | Hunts U15's Cup | 2018-19 | N/A |
| 2018-10-28 12:00:58October 28, 2018 | St Ives Town U15 | 1*(3) - 1 (2) |  Stowmarket Town U15 | 12:00:5812:00 | U15 Challenge Cup | 2018-19 | N/A |
| 2018-11-04 11:00:52November 4, 2018 | Wroxham U15  | 3 - 3 | St Ives Town U15 | 11:00:5211:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-11-11 12:00:46November 11, 2018 | Haverhill Rovers U15 | 3 - 1 | St Ives Town U15 | 12:00:4612:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-11-18 12:00:47November 18, 2018 | St Ives Town U15 | 2 - 1 |  Needham Market U15 | 12:00:4712:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-11-25 10:30:17November 25, 2018 | St Ives Town U15 | 4 - 1 |  Newmarket Town U15 | 10:30:1710:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-12-02 10:30:17December 2, 2018 | St Ives Town U15 | 0 - 1 | AFC Sudbury U15 | 10:30:1710:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2018-12-09 12:00:46December 9, 2018 | St Ives Town U15 | 3 - 1 |  Norsemen U15 | 12:00:4612:00 | U15 Challenge Cup | 2018-19 | N/A |
| 2018-12-16 10:30:26December 16, 2018 | St Ives Town U15 | 3 - 0 | Stowmarket Town U15 | 10:30:2610:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-01-06 12:45:40January 6, 2019 | Newmarket Town U15 | 3 - 5 | St Ives Town U15 | 12:45:4012:45 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-01-13 11:00:37January 13, 2019 | St Ives Town U15 | 1 - 1 | Wroxham U15 | 11:00:3711:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-01-27 11:00:41January 27, 2019 | St Ives Town U15 | 2 - 1 |  Walsham Le Willows U15 | 11:00:4111:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-02-10 11:00:37February 10, 2019 | Stowmarket Town U15 | 2 - 2 | St Ives Town U15 | 11:00:3711:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-03-03 10:30:24March 3, 2019 | Takeley U15  | 2 - 4 | St Ives Town U15 | 10:30:2410:30 | U15 Challenge Cup | 2018-19 | N/A |
| 2019-03-17 16:00:34March 17, 2019 | Needham Market U15 | 1 - 3 | St Ives Town U15 | 16:00:3416:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-03-24 12:00:32March 24, 2019 | Billericay Town U15  | 8 - 2 | St Ives Town U15 | 12:00:3212:00 | U15 Challenge Cup | 2018-19 | N/A |
| 2019-03-31 10:30:24March 31, 2019 | Walsham Le Willows U15 | 0 - 3 | St Ives Town U15 | 10:30:2410:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-04-07 10:30:29April 7, 2019 | St Ives Town U15 | 3 - 3 |  Felixstowe & Walton U15’s | 10:30:2910:30 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-04-14 11:00:05April 14, 2019 | St Ives Town U15 | 3 - 1 | Haverhill Rovers U15 | 11:00:0511:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |
| 2019-04-28 11:00:25April 28, 2019 | Felixstowe & Walton U15’s | H - W | St Ives Town U15 | 11:00:2511:00 | Eastern Junior Alliance U15 Green | 2018-19 | N/A |