Ange Postecoglou takes his seat in the Tottenham Hotspur Stadium dugout for the first time when the Lilywhites welcome Shakhtar Donetsk to North London for their penultimate friendly on Sunday.
The charity match will see funds raised for the people of Ukraine amid the ongoing Russian invasion, although Tottenham may also take the opportunity to repair their relationship with Shakhtar following the controversial Manor Solomon transfer.
Match preview
Before Bayern Munich chiefs arrived in North London attempting to find common ground with cut-throat Tottenham chairman Daniel Levy - to no avail - the Bavarians' top target Harry Kane did what he does best in Singapore to propel Spurs to their opening pre-season victory on July 26.
Taking on three-time national champions Lion City Sailors after a proposed meeting with Roma fell through, Postecoglou picked up his first victory as Tottenham head coach in a 5-1 thumping, during which Kane opened his pre-season account alongside a Richarlison hat-trick and Giovani Lo Celso strike.
Tottenham's demolition job of the Singapore outfit was only their second exhibition game of the summer following their opening 3-2 defeat to West Ham United, as torrid conditions led to the late postponement of their clash with Leicester City in Thailand, and Spurs must now navigate two friendlies in the space of as many days.
Following Sunday's affair, Postecoglou's side will embark on a trip to Catalonia to face Barcelona in the Joan Gamper Trophy final, before kicking off a new Premier League era away to London rivals Brentford on August 13.
The in-demand Kane has supposedly decided that he will continue in Tottenham colours if Bayern have not reached an agreement for his signature before Spurs' Premier League opener, but the Lilywhites will soon welcome 19-year-old Rosario Central striker Alejo Veliz to the club, where he will reinforce Postecoglou's attacking ranks alongside former Shakhtar wing king Solomon.
As conflict continues to rage in Eastern Europe, Shakhtar were left powerless to a FIFA ruling allowing Solomon - who enjoyed a brief period of success during a loan spell with Fulham last season - to suspend his contract and leave on a free transfer to the Tottenham Hotspur Stadium.
Seething Shakhtar CEO Sergei Palkin memorably threatened Tottenham with legal action should they bring Solomon back to the Premier League, but any tense exchanges over transfers should not dampen the occasion this weekend, as the visitors boost the coffers of their charitable foundation 'Shakhtar Social' to help those affected by the devastating war.
While there was no Ukrainian Cup or Ukrainian Super Cup last season, Shakhtar once again asserted their dominance in the top flight to come away with a 14th top-flight title, gleaning 72 points to finish five clear of Dnipro-1 and Zorya Luhansk.
As a result, another Champions League group-stage spot awaits after Shakhtar bowed out at the first hurdle in last year's competition - but not without a 4-1 thumping of RB Leipzig to their name - and Patrick van Leeuwen's side have already taken four points from their opening two Ukrainian Premier League fixtures this season.
Tottenham and Shakhtar will be renewing hostilities 14 years on from their inaugural meeting in the 2008-09 UEFA Cup last 16, where the Ukrainian giants stormed to a 2-0 win in the first leg, and a 1-1 home draw seven days later was not enough to save Spurs' European bacon.
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