Head-to-head
Aggregate
All meetings
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 05 Jun 2025 | Singapore | 3–1 | Maldives | H | ITL · Friendly |
| 17 Dec 2022 | Singapore | 3–1 | Maldives | H | ITL · Friendly |
| 23 Mar 2018 | Singapore | 3–2 | Maldives | H | ITL · Friendly |
| 04 Mar 2003 | Singapore | 4–1 | Maldives | H | ITL · Friendly |
| 09 Apr 2002 | Singapore | 2–0 | Maldives | H | ITL · Friendly |
| 07 Jul 1996 | Singapore | 5–2 | Maldives | H |
|
| 29 Jun 1996 | Maldives | 0–2 | Singapore | A |
|