| 12-Feb-1900 | Friendly | - | H | W | 7 - 2 | Raby, Pratt (4), Copeland, Kirwan | TOTTENHAM HOTSPUR v CHESTERFIELD | |||||||||
| 17-Oct-08 | Division 2 | 14,000 | H | W | 4 - 0 | Walton, Minter (2), Steel R | Competition | P | W | D | L | F | A | |||
| 08-Mar-09 | Division 2 | 5,000 | A | W | 3 - 1 | Woodward, Middlemiss (2) | FLD2 (old) | 20 | 9 | 6 | 5 | 45 | 28 | |||
| 03-Oct-31 | Division 2 | 15,192 | A | L | 2 - 4 | Brain, Bellamy | FA Cup | 2 | 1 | 1 | 0 | 4 | 3 | |||
| 13-Feb-32 | Division 2 | 21,591 | H | D | 3 - 3 | Davies, Hunt GS, Evans W | Friendlies | 2 | 2 | 0 | 0 | 11 | 4 | |||
| 19-Nov-32 | Division 2 | 24,584 | H | W | 4 - 1 | O'Callaghan, Evans W (3, 1pen) | Total Games | 24 | 12 | 7 | 5 | 60 | 35 | |||
| 17-Mar-33 | Division 2 | 10,631 | A | D | 1 - 1 | Morrison | Tottenham's record against Chesterfield 64.58% | |||||||||
| 14-Nov-36 | Division 2 | 30,054 | H | W | 5 - 1 | Hunt GS (3, 2pens), Morrison, Miller | ||||||||||
| 20-Mar-37 | Division 2 | 13,621 | A | W | 3 - 1 | McCormick (3) | UK Soccer Shop | |||||||||
| 30-Oct-37 | Division 2 | 16,092 | A | D | 2 - 2 | Ward (pen), Morrison | SubSide Football Kits | |||||||||
| 12-Feb-38 | F.A. Cup 5 | 30,561 | A | D | 2 - 2 | Gibbons, Miller | TOFFS Retro Football Shirts | |||||||||
| 16-Feb-38 | F.A. Cup 5 Replay | 36,994 | H | W | 2 - 1 | Sargent, Morrison | My Football Facts Home Page | |||||||||
| 12-Mar-38 | Division 2 | 20,915 | H | W | 2 - 0 | Sargent, Miller | My Football Facts Spurs Page | |||||||||
| 26-Nov-38 | Division 2 | 24,434 | H | D | 2 - 2 | Whatley (pen), Ludford | ||||||||||
| 01-Apr-39 | Division 2 | 15,285 | A | L | 1 - 3 | Spelman | ||||||||||
| 07-Dec-46 | Division 2 | 38,654 | H | L | 3 - 4 | Bennett, Cox (2) | ||||||||||
| 12-Apr-47 | Division 2 | 14,802 | A | D | 0 - 0 | |||||||||||
| 25-Dec-47 | Division 2 | 44,863 | H | W | 3 - 0 | Baily, Duquemin, Bennett | ||||||||||
| 27-Dec-47 | Division 2 | 19,495 | A | L | 1 - 3 | Burgess | ||||||||||
| 04-Sep-48 | Division 2 | 46,804 | H | W | 4 - 0 | Cox, Baily (2), Jones | ||||||||||
| 15-Jan-49 | Division 2 | 15,861 | A | L | 0 - 1 | |||||||||||
| 26-Dec-49 | Division 2 | 41,879 | H | W | 1 - 0 | Ramsey (pen) | ||||||||||
| 27-Dec-49 | Division 2 | 26,341 | A | D | 1 - 1 | Scarth | ||||||||||
| 24-Jul-85 | Friendly | - | A | W | 4 - 2 | Roberts, Waddle (2), Chiedozie | ||||||||||