Chelsea have played AFC Ajax 3 times in competitive football, winning 2, drawing 1 and losing 0, first meeting on 23 Oct 2019 and most recently on 22 Oct 2025. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 23 Oct 2019 | 2019–20 | Champions League | A | AFC Ajax | 1–0 | Michy Batshuayi 86 | 52,482 |
| 5 Nov 2019 | 2019–20 | Champions League | H | AFC Ajax | 4–4 | Jorginho 5, César Azpilicueta 63, Jorginho 71, Reece James 74 | 39,132 |
| 22 Oct 2025 | 2025–26 | Champions League | H | AFC Ajax | 5–1 | Marc Guiu 18, Moisés Caicedo 27, Enzo Fernández 45, Tyrique George 48, Estêvão Willian 45+6 | 38,948 |