Following Friday's draw for the knock-out stages of the Europa League, Postecoglou discovered the first hurdle will be Dutch side AZ Alkmaar in the last-16.
The good news for Postecoglou is that his side have already beaten Alkmaar in this season's group stage, Richarlison's second-half penalty giving them a 1-0 home victory in October when the visitors had defender David Moller Wolfe sent off with five minutes left.
If Spurs can overcome the side who are currently in fifth place in the Eredivisie, they would then face a difficult-looking quarter-final against either another Dutch side, league leaders Ajax, or German side Eintracht Frankfurt, currently third in the Bundesliga.
Victory in that one would set up a semi-final against one of four possible opponents - Norwegian champions FK Bodo/Glimt who'll play Greek side Olympiacos, or Czech team Viktoria Plzen who meet Italian serie A side Lazio in their last-16 ties.
It's certainly not the easiest route for Postecoglou, who now has just Europe's second-string tournament left to keep up the record he pointed out earlier this term - that he always wins a trophy in his second season at a club.
Spurs eased into the last-16 by finishing a comfortable fourth in the extended group stage, while Alkmaar look as if they'll be tough again after making it through the playoffs, drawing 2-2 at Turkish side Galatasaray on Thursday for an impressive 6-3 aggregate victory.
Spurs have been installed by British bookmakers as favourites to win the trophy, just ahead of fellow Premier League strugglers Manchester United, who are on the other side of the draw.
United have been drawn against Spanish side Real Sociedad - their third meeting in five seasons in the competition - while Scottish giants Rangers have an eye-catching date with Jose Mourinho's Turkish outfit Fenerbahce.
Roma and Lazio had faced the possibility of a Rome derby at Stadio Olimpico, but they've been kept apart.
Roma have been drawn against another fancied side Athletic Bilbao, whose stadium hosts the final on May 21.
EUROPA LEAGUE LAST-16 DRAW (Two legs, March 6 and March 13)
Viktoria Plzen (Czech Republic) v Lazio (Italy)
Bodo/Glimt (Norway) v Olympiacos (Greece)
Ajax Amsterdam (Netherlands) v Eintracht Frankfurt (Germany)
AZ Alkmaar (Netherlands) v Tottenham Hotspur (England)
Roma (Italy) v Athletic Bilbao (Spain)
Fenerbahce v Rangers
FCS Bucharest (Romania) v Lyon (France)
Real Sociedad (Spain) v Manchester United (England)
QUARTER-FINALS (April 10 and April 17)
QF1: Bodo/Olympiacos v Plzen/Lazio
QF2: AZ/Tottenham v Ajax/Frankfurt
QF3: Fenerbahce/Rangers v Roma/Bilbao
QF4: Bucharest/Lyon v Sociedad/Man Utd
SEMI-FINALS (May 1 and May 8)
Semi-final 1: QF2 winners v QF1 winners
Semi-final 2: QF3 winners v QF4 winners
FINAL (Bilbao, May 21)
