Chelsea have played VfB Stuttgart 3 times in competitive football, winning 2, drawing 1 and losing 0, first meeting on 13 May 1998 and most recently on 9 Mar 2004. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 13 May 1998 | 1997–98 | Cup Winners' Cup | H | VfB Stuttgart | 1–0 | Gianfranco Zola | 30,216 |
| 25 Feb 2004 | 2003–04 | Champions League | A | VfB Stuttgart | 1–0 | Fernando Meira 12 | 50,000 |
| 9 Mar 2004 | 2003–04 | Champions League | H | VfB Stuttgart | 0–0 | 36,660 |