Villa have managed to win just once this season, with a 1-0 opening day victory over Bournemouth, and Sherwood is certainly under pressure just over two months in to the season.
Villa's problems this term aren't all Sherwood's fault; losing Fabian Delph and Christian Benteke over the summer was never going to be easy, but with 13 summer signings arriving and few of them adjusting to life at Villa Park quickly, it's been tough for Sherwood to build a steady, solid outfit.
This weekend, Villa face an out-of-form Swansea side who lost 1-0 at home to Stoke City on Monday night, and many believe that it could be the defining fixture in Sherwood's future at Villa Park.
Sky Sports pundit Phil Thompson also believes that it could be made or break for Sherwood this weekend, and admited that he fears for Villa this season based on their poor performances this season, whilst also questioning the club's transfer policy over the summer.
"It is a must-win for him," said Thompson. "I think it would be absolutely crazy [to sack him]. For what he did last year; getting to the cup final, saving them from relegation...we say about the transfer activity - what happened? He's been in a difficult position, and these are difficult times, but from what I've watched, I do fear for this side," he added.
Villa signed young players with potential such as Jordan Amavi, Jordan Veretout, Jordan Ayew and Adama Traore, so expecting an instant impact would have been naive.
However, Sherwood desperately needs a result to get some confidence in himself as well as in his players, and there may not be a better opportunity to do it than against a struggling Swansea side this weekend.