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
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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.
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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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Team News
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Tottenham have a new long-term absentee in their medical bay for the next couple of months, as Spanish attacker Bryan Gil has undergone surgery on a groin injury, although the 22-year-old has only been a peripheral figure during his time in North London so far.
Gil has become the second Lilywhites player to go under the knife this summer following Ryan Sessegnon (hamstring), while Rodrigo Bentancur - who injured his ACL six months ago - is still several weeks away from a first-team comeback. On a brighter note, Postecoglou eased concerns over Yves Bissouma's fitness after the midfielder appeared to damage his ankle last time out.
With only 48 hours to recover for a journey to Barcelona, Postecoglou is sure to make use of his entire squad over the next few days, and the Australian could very well restrict his more revered names to a 30 or 45-minute run-out ahead of the Joan Gamper Trophy.
Similarly, Shakhtar also have a trio of injury concerns bedevilling them, as Georgiy Sudakov (appendicitis), Valeriy Bondar (collarbone fracture) and Ivan Petryak (ankle) are all sidelined for the time being.
Midfielder Artem Bondarenko was sent off during the visitors' recent 1-1 draw with NK Veres Rivne in the league, but the 22-year-old's participation here is unaffected, while ex-Ajax attacker Lassina Traore should operate at the tip of the attack.
Tottenham Hotspur possible starting lineup:
Austin; Emerson, Romero, Davies, Reguilon; Sarr, Skipp, Lo Celso; Solomon, Richarlison, Perisic
Shakhtar Donetsk possible starting lineup:
Trubin; Gocholeishvili, Kozik, Matvienko, Pedrinho; Bondarenko, Castillo; Zubkov, Sikan, Newerton; Traore
We say: Tottenham Hotspur 2-1 Shakhtar Donetsk
The result of Sunday's game will pale into insignificance as both sets of players come together for a good cause, but with Shakhtar already in the thick of their domestic season, the visitors' minds may be elsewhere.
Postecoglou's side should also have one eye on their impending date with Barcelona, and while it remains to be seen how the hosts will set up for the charity friendly, we can envisage a Lilywhites success either way.
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