Spurs boss Ange Postecoglou has learned his side's treacherous path towards winning the trophy that could yet provide a glorious finish to what's been a difficult season for the Australian.
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.