March is shaping up to be quite a month for Spurs as they continue their search for a top-four finish and Europa League success.
Chelsea, Arsenal, Southampton and Liverpool all await Sherwood's men in the Premier League, while they also face a two-legged Europa League tie with Benfica.
The first leg of the last-16 clash comes after this weekend's trip to Stamford Bridge - somewhere Spurs have not won since Gary Lineker and David Howells netted in a 2-1 victory in February 1990.
This would certainly be a timely moment for Tottenham to end that hoodoo and Sherwood is quietly confident of upsetting the apple cart on Saturday.
"We're not frightened of this period, we're looking forward to it," he said.
"We're going in with the pressure off us. Obviously what has happened in the past we have to put to the back of our minds.
"We have to go there and impose ourselves and hopefully we can get a positive result, but there is absolutely no pressure on the boys, is there?
"Our record is so bad that we can go there and take the shackles off and enjoy the day. The only people that expect us to win are inside our dressing room."
The long wait for a win in west London is compounded by the fact Jose Mourinho remains unbeaten in 74 league matches at Stamford Bridge.
Sherwood is in awe of that "incredible" record - "I can't understand why Chelsea fans like him so much," he said with a smile - and was quick to praise the job the Portuguese for the job he has done since his return.
Chelsea are four points clear at the top as the season enters the home straight, although the Spurs head coach does expect them to fall short this season.
"I think Man City are still favourites to win the league, even though Chelsea will push them all the way," Sherwood said.
"They have got the games in hand and I just think that the fact they score so many goals gives them the edge."
Sherwood highlighted Eden Hazard as one of the "genuinely world-class" players Spurs need to nullify on Saturday if they are to keep their fine away form on track.
Tottenham's 29-point haul represents the Premier League's best record on the road this term, but they fell to a poor 1-0 defeat to relegation-threatened Norwich last time they played away from White Hart Lane.
"We've been good away from home but obviously our recent away game was poor," Sherwood said.
"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."
Kyle Walker, Younes Kaboul and Zeki Fryers will all be assessed ahead of the match - rare good news on the injury front for Spurs.
Christian Eriksen, Danny Rose, Etienne Capoue, Vlad Chiriches and Erik Lamela are all definitely absent, although Sherwood was quick to dismiss speculation that the latter is out for the rest of the campaign.
"We're hoping he'll be back before the end of the season," Sherwood said.
"But I don't think he is anywhere near resuming training or being up for selection."