| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 5/8/22 | Chelsea U23 vs Tottenham Hotspur U23 | Premier League 2 - Promotion - Play Offs | 2:1 | Yes | Yes |
| 8/16/21 | Tottenham Hotspur U23 vs Chelsea U23 | Premier League 2 - Promotion - Play Offs | 2:2 | Yes | Yes |
| 4/18/21 | Tottenham Hotspur U23 vs Chelsea U23 | Premier League 2 - Promotion - Play Offs | 1:4 | Yes | Yes |
| 12/14/20 | Chelsea U23 vs Tottenham Hotspur U23 | Premier League 2 - Promotion - Play Offs | 3:2 | Yes | Yes |
| 1/6/20 | Tottenham Hotspur U23 vs Chelsea U23 | Premier League 2 - Promotion - Play Offs | 0:1 | No | No |
| 8/30/19 | Chelsea U23 vs Tottenham Hotspur U23 | Premier League 2 - Promotion - Play Offs | 2:2 | Yes | Yes |
| 3/1/19 | Tottenham Hotspur U23 vs Chelsea U23 | Premier League 2 - Promotion - Play Offs | 1:1 | No | Yes |
| 11/23/18 | Chelsea U23 vs Tottenham Hotspur U23 | Premier League 2 - Promotion - Play Offs | 1:1 | No | Yes |