Tottenham Hotspur will face Sky Bet Championship opposition in Coventry City in the Third Round of the Carabao Cup, having been drawn away to the Sky Blues.
The tie will take place at the Coventry Building Society Arena and will be played the week commencing 16th September, with exact details to be announced in due course. The cup clash comes sandwiched between Premier League home matches with Arsenal and Brentford.
This will be Spurs' first trip to the CBS Arena stadium, having played and beaten Coventry at their old Highfield Road ground in September 2003 - a 0-3 victory in the League Cup.
In the past two seasons, The Lilywhites have failed to reach the Fourth Round of this competition, losing at Fulham on penalties in Round Two last time out, and at Nottingham Forest at this stage of the competition the season before that.
Throughout the previous four editions of the Carabao Cup, Tottenham have been drawn against non-Premier League opposition just once at this stage - that came in 2020. Spurs were pitted to face Leyton Orient, but the tie never took place, with the North Londoners given a bye due to The O's having COVID cases amongst the group.
Familiar face returning
James Maddison will be returning to his old stomping ground, having progressed through the ranks at the Coventry Building Society Arena as a youth player.
The Englishman made his City first-team debut in 2014, coming off the bench during a League Cup clash with Cardiff City, before making his first start, as an 18-year-old, two games later. During that game, he scored his first-ever professional goal and one month later, he put pen to paper on his first professional contract.
Two years later, after scoring four goals in 24 appearances, the attacking midfielder made the switch to Norwich City, although he was immediately loaned back to his boyhood club for the 2015/16 season.
Maddison has played against his former club on just one occasion throughout his career, and that came whilst in East Anglia, and funnily enough, in this exact competition too. During the 6-1 rout, the ex-Coventry man registered two assists.
Old foes reunite
Tottenham and Coventry have plenty of history in cup competitions.
In the 1987 FA Cup Final, the Sky Blues pipped David Pleat's men with an extra-time victory, following Gary Mabbutt's 96th-minute own goal, as 96,000 people crammed into the Old Wembley Stadium.
The Lilywhites went ahead after two minutes through Clive Allen but David Bennett equalised seven minutes later. Gary Mabbutt regained the advantage four minutes before the break, but just after the hour mark Spurs were pegged back for the second time as Keith Houchen scored for Coventry City. In extra time, Mabbutt was on the scoresheet again, but this time at the wrong end, meaning his side succumbed to a defeat.
These two sides last met in the cup eleven years ago, with the Premier League side winning 3-0 in an FA Cup Third Round tie - a Clint Dempsey brace and Gareth Bale strike enough to secure a safe passage through to the next stage.
Spurs' mixed League Cup fortunes
The Carling Cup was the last trophy the club won, way back in 2008 - a measly sixteen years ago.
A Jonathan Woodgate goal in extra-time saw Spurs beat fierce London rivals Chelsea by two goals to one after Dimitar Berbatov's 70th-minute penalty had cancelled out Didier Drogba's first-half opener.
Since the victorious run during the 2007/08 season, The Lilywhites have lost three finals in this competition, and have made it to within one step from Wembley on two other occasions. The final defeats came against both Manchester clubs in 2009 and 2021, and Chelsea in 2015.
However, one of the worst moments for Tottenham in this competition, and one of the most embarrassing nights in the club's history, came under Mauricio Pochettino in September 2019.
The Argentinian tactician fielded a heavily weakened side as Spurs made the trip to Essex to take on Colchester United, and the U's held their gargantuan opponents all the way to a penalty shootout. Christian Eriksen and Lucas Moura failed to score, meaning the League Two outfit produced one of the greatest shocks the competition has ever seen.
Spurs will be looking to avoid a potential banana skin at the Coventry Building Society Arena in September.