Tottenham, conquerors of Champions League holders Inter Milan in midweek, had to settle for second best in a 4-2 defeat at the Reebok Stadium despite a rousing comeback.
Trailing 3-0 they scored twice in the last 11 minutes thanks to Alan Hutton and substitute Roman Pavlyuchenko.
But Martin Petrov stepped off the bench to seal Bolton's victory in stoppage time with a fine solo effort.
Tottenham have never achieved a league victory at the ground and manager Harry Redknapp will wonder how they failed to build on their famous win in midweek.
Certainly they missed Rafael van der Vaart and Aaron Lennon, who are both suffering from hamstring injuries, but Bolton were good value for their victory with Kevin Davies scoring twice, once from the penalty spot, and Gretar Steinsson also on target.
Tottenham were left reeling but pulled a goal back in the 79th minute thanks to a magnificent solo effort from Alan Hutton and were given real hope when Pavlyuchenko grabbed a second with a superb volley nine minutes later - only for substitute Petrov to wrap things up.