Having browsed through the book, SPURS: Day-TO-Day Life at White Hart Lane by Graham Betts, on many occasions for this daily up-date and other snippets of Spurs history, I doubt if there are many poorer days.
Prepare yourself for the bad news:
1897 Luton (h) Lost 1-2
1909 WBA (h) 2nd Div. Lost 1-3
1912 WBA (a) 1st Div. Lost 0-2
1915 Bradford Park Avenue (a) 1st Div. Lost 1-5
1920 West Ham (a) 2nd Div. Lost 1-2 [Spurs finished Champions with 70 pts and only lost 4 games all season]
1926 Leicester City (h) 1st Div. Lost 1-3
1948 Blackpool (Villa Park) FA Cup SF Lost 1-3 (aet)
1954 WBA (a) FA Cup 6th R. Lost 0-3
1957 Arsenal (h) 1st Div. Lost 1-3
1982 Liverpool (Wembley) L.Cup Final Lost 1-3 (aet) First defeat at Wembley
2002 Chelsea (a) Prem. Lost 0-4
2005 Newcastle Utd (a) FA Cup 6th R. Lost 0-1 (Rob Styles Day in Newcastle - when he disallowed a Spurs goal and refused them 2 obvious penalties)
Am I depressed after recording all of that?
There was some Good News - Not a lot:
1965 Blackpool (h) 1st Div. Won 4-1 Mullery, Robertson, Greaves, Jones
1971 Chel$ki (h) 1st Div. Won 2-1 Chivers, Peters
1976 Aston Villa (h) 1st Div. Won 5-2 McAllister, Perryman, Duncan, Robinson, opp.og
1999 Aston Villa Prem. Won 1-0 Sherwood
Going on this record Spurs should consider refusing to play on this date ever again.