Spurs have not won in west London since Gary Lineker scored the winner in 1990 and travel there in fifth place - six points behind second-placed Liverpool - looking to establish their top-four credentials ahead of a busy run-in.
History may be against Tottenham, but they do boast the best away record in the Premier League this season and Sherwood says his team will play with freedom in the Saturday Night Football clash.
"What's happened in the past we have to put to the back of our minds," he said. "We have to go there and impose ourselves and hopefully get a positive result.
"But there's absolutely no pressure on the boys because our record there is so bad, so we can go there, take the shackles off and enjoy the day.
"The only people who expect us to win are inside our dressing room.
"We've been good away from home but obviously our recent away game was poor. We played Norwich and we got beaten. If we play anything like we did at Norwich they will be putting more bulbs in the scoreboard.
"But we need to make sure that we're a lot better than that and we will be. The motivation of the players is there, the record suggests that.
"We're going to go up there and give it everything. It's a chance for them to put themselves in the record books and we're confident that we can spring a surprise, because after all it is going to be a surprise isn't it, if we beat Chelsea at the Bridge."
Spurs' hoodoo is not the only record standing in the way of three valuable points in their bid for the top four, with Chelsea boss Jose Mourinho defending a 74-game unbeaten run in the league at Stamford Bridge.
"It's incredible. I can't understand why the Chelsea fans like him so much," added Sherwood with a smile.
"He knows how to win. If he can entertain and win then good, but the more important thing for Mourinho is to get the three points and invariably he does that.
"They're top of the league and they have players in the squad who know how to win. He has a fantastic record."