Home History
| Singapore Premier League | 2023/07/20 11:45 | Lion City Sailors FC v Tanjong Pagar United | W | 3-2 |
| Singapore Premier League | 2023/07/16 10:00 | Albirex Niigata Singapore v Lion City Sailors FC | L | 3-1 |
| Singapore Premier League | 2023/07/11 11:45 | Lion City Sailors FC v DPMM FC | L | 1-3 |
| Singapore Premier League | 2023/07/07 11:45 | Young Lions v Lion City Sailors FC | W | 0-4 |
| Singapore Premier League | 2023/07/01 10:00 | Tanjong Pagar United v Lion City Sailors FC | W | 1-7 |
| Singapore Premier League | 2023/06/25 10:00 | Lion City Sailors FC v Hougang United FC | W | 3-0 |
| Singapore Premier League | 2023/06/10 10:00 | Lion City Sailors FC v Young Lions | W | 4-1 |
| Singapore Premier League | 2023/06/07 11:45 | Lion City Sailors FC v Tampines Rovers FC | D | 1-1 |
Away History
| Elite Club Friendlies | 2023/07/18 10:00 | Tottenham v West Ham | L | 2-3 |
| England Premier League | 2023/05/28 15:30 | Leeds v Tottenham | W | 1-4 |
| England Premier League | 2023/05/20 11:30 | Tottenham v Brentford | L | 1-3 |
| England Premier League | 2023/05/13 14:00 | Aston Villa v Tottenham | L | 2-1 |
| England Premier League | 2023/05/06 14:00 | Tottenham v Crystal Palace | W | 1-0 |
| England Premier League | 2023/04/30 15:30 | Liverpool v Tottenham | L | 4-3 |
| England Premier League | 2023/04/27 19:15 | Tottenham v Man Utd | D | 2-2 |
| England Premier League | 2023/04/23 13:00 | Newcastle v Tottenham | L | 6-1 |