Tottenham Hotspur have played Chester 2 times in competitive football, winning 2, drawing 0 and losing 0, first meeting on 20 Sep 1995 and most recently on 4 Oct 1995. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 20 Sep 1995 | 1995–96 | League Cup | H | Chester | 4–0 | Chris Armstrong, Chris Armstrong, Ronny Rosenthal, Teddy Sheringham | 17,645 |
| 4 Oct 1995 | 1995–96 | League Cup | A | Chester | 3–1 | Teddy Sheringham, Teddy Sheringham, David Howells | 5,372 |
All Tottenham Hotspur head-to-head records · Tottenham Hotspur season by season