Sunday's game will be a repeat of Liverpool's 5-0 massacre of Tottenham at White Hart Lane earlier in the season if Sherwood is not careful.
Tottenham have continually played a high defensive line this season and it has been to their detriment. Andre Villas Boas paid for employing such tactics with the 5-0 thrashing from Liverpool in what proved to be his last game in charge for Spurs.
The introduction of Tim Sherwood as Boas' replacement however did not yield a change in defensive approach. Sherwood has largely stuck to keeping the back four stationed high up the pitch.
And if he does the same against Liverpool he would have learned nothing from Boas' experience in the reverse fixture back in December.
So for Tottenham to play further up the pitch at Anfield can only be a bad idea. Liverpool have shown they are ever so deadly and clinical when given space and Sunday's match-up has the potential to expose Sherwood's tactical naivety as much as Boas's.
The pace of Daniel Sturridge and Raheem Sterling, coupled with Luis Suarez's determined, hard running and Philippe Coutinho or Steven Gerrard's delicate through balls make for dangerous combination play. Such play will only be magnified if there is oceans of room to move into and manoeuvre in.
While it is not wise to suggest the visitors sit deep to try to counteract this, as Sunderland did on Wednesday, the alternative to a high line must surely be to get the balance right.
Yet Sherwood appears to be just as stubborn as his predecessor so that particular compromise may not see the light of day, either in the trip to Anfield or in fact any of the games left in Spurs' season.
Would Tim Sherwood be making a mistake in playing a high line against Liverpool?