| USA USL League Two | 07/16 23:00 | 1 |
The Villages
v
Caledonia SC
|
L | 3-2 | |
| USA USL League Two | 07/13 23:00 | 1 |
Caledonia SC
v
FC Miami City
|
- | Cancelled | |
| USA USL League Two | 07/06 22:00 | 1 |
[4] FC Miami City
v
Caledonia SC
[8] |
L | 7-1 | |
| USA USL League Two | 06/26 22:00 | 1 | [6] Miami AC v Caledonia SC [7] | L | 2-1 | |
| USA USL League Two | 06/25 19:00 | 1 | FC Florida U23 v Caledonia SC | L | 3-0 | |
| USA USL League Two | 06/22 22:00 | 1 |
[9] Weston FC
v
Caledonia SC
[7] |
L | 1-0 | |
| USA USL League Two | 06/11 23:00 | 1 |
Florida Elite
v
Caledonia SC
|
L | 3-0 | |
| USA USL League Two | 06/08 23:30 | 1 | [7] Tampa Bay United v Caledonia SC [4] | L | 3-0 | |
| USA USL League Two | 06/04 18:00 | 1 |
Weston FC
v
Caledonia SC
|
- | Postponed | |
| USA USL League Two | 06/01 23:00 | 1 |
Caledonia SC
v
The Villages
|
L | 0-2 | |
| USA USL League Two | 05/28 23:00 | 1 | Caledonia SC v FC Florida U23 | W | 1-0 | |
| USA USL League Two | 05/24 23:30 | 1 | Caledonia SC v Nona FC | L | 0-3 | |
| USA USL League Two | 05/21 20:00 | 1 |
Caledonia SC
v
Weston FC
|
W | 1-0 | |
| USA USL League Two | 05/14 23:00 | 1 | Caledonia SC v Tampa Bay United | L | 0-4 | |
| USA USL League Two | 05/11 23:45 | 1 |
Caledonia SC
v
Florida Elite
|
D | 1-1 |