Spurs head coach Sherwood has come under fire following three successive high-profile defeats in the past fortnight, including a 3-1 reverse to Jorge Jesus' Primeira Liga leaders in the first leg of their last-16 tie at White Hart Lane last Thursday.
That setback was sandwiched with a 4-0 rout at the hands of Chelsea at Stamford Bridge before Tottenham suffered north London derby heartbreak in a 1-0 home loss to rivals Arsenal on Sunday.
Sherwood will now seek solace in this week's second leg, but the visitors face what appears a near impossible task in overturning the deficit at Estadio da Luz.
Benfica are unbeaten in 10 European home games, their last loss coming in a 2-0 setback to Barcelona in 2012 in the UEFA Champions League group stages. The Portuguese team have also yet to taste defeat on home soil in the UEFA Europa League in 16 outings since the competition replaced the previous UEFA Cup format in 2009.
The fixture will carry extra spice from the first leg after Sherwood accused opposite number Jesus of showing "a lack of class", when he appeared to signal the number of goals his side had scored when he held three fingers aloft.
Despite the difficulty of the task and Tottenham's recent setbacks suggesting otherwise, winger Andros Townsend is confident of progressing to the quarter-finals.
Speaking to the club's official website, he said: "It's another big game on Thursday. There is still a lot to play for.
"We've got nothing to lose. We're two goals behind from the home leg, so we can go there, have a go and see what happens."
In contrast to Tottenham's woes, Benfica have been seemingly unstoppable and have not tasted defeat in any competition since a 1-0 loss to Olympiacos in the Champions League at the start of November.
Only once have Benfica been beaten in the Primeira Liga this season and their march towards the title shows no signs of stopping, with second-placed Sporting Lisbon seven points adrift.
Both sides have a centre-back suspended, with Tottenham's Jan Vertonghen and Benfica's Silvio the players to miss out.