Tottenham Round-Up, Friday 23rd October 2026: De Zerbi Delivers Chelsea Team News as Maddison Doubt Confirmed
All eyes are on Saturday's trip to Stamford Bridge, with Roberto De Zerbi holding his pre-match press conference on Friday afternoon. The Spurs boss gave a full fitness update on his squad, with James Maddison flagged as a doubt for the derby (Football.London) (Football.London) (Spurs Web) (Football.London) (TottenhamHotspur.com) (TottenhamHotspur.com). Football.London report that De Zerbi's update actually brought a triple injury boost elsewhere in the squad despite the Maddison concern, in a ten-player round-up (Football.London). Spurs Web add that the head coach also addressed the futures of Kulusevski and others during his session with the media (Spurs Web) (Football.London).
Team news elsewhere points to a selection headache at left-back, with both Destiny Udogie and Andy Robertson doubtful for the Chelsea game, leaving De Zerbi to consider alternative options - each with its own drawback, according to Spurs Web (Spurs Web) (Spurs Web). Sports Mole and Football.London both carry fuller injury and suspension round-ups ahead of kick-off, with Football.London suggesting as many as twelve players could be missing once a "double injury hint" is factored in (Sports Mole) (Football.London). On the lineup front, Football.London report that Maddison's fitness issue could force a midfield rethink from De Zerbi (Football.London). Ahead of the trip to Stamford Bridge, De Zerbi has also urged his players to use Tottenham's poor record at the ground as extra motivation (Spurs Web). Looking slightly further ahead, Tottenham's official site also confirmed Naz is back in contention for the following north London derby (TottenhamHotspur.com), while Djed Spence has said the squad need to "fix a few things" as they look to build momentum (TottenhamHotspur.com).
Fan opinion has been split on one selection call in particular, with a Football.London poll of more than 1,700 Spurs supporters asked whether Dejan Kulusevski should start against Chelsea (Football.London). Elsewhere, Football365 report that Tottenham's best player has reportedly soured on De Zerbi and the project at the club, with suggestions he could push for a move to Real Madrid or Barcelona, though Football365 say Spurs have responded to those claims (Football365). GiveMeSport, meanwhile, argue the club should consider selling a previously "untouchable" star alongside Richarlison (GiveMeSport).
On the transfer front, Sports Mole report that Tottenham have placed a "big price tag" on Pedro Porro amid reported interest from Real Madrid and Barcelona (Sports Mole). Spurs Web say Tottenham and Aston Villa are among those monitoring a highly-rated Brentford striker following his strong 2025/26 campaign (Spurs Web), while another Spurs Web report claims the club have been told now could be the right time to move for a prolific Bundesliga forward they have been scouting (Spurs Web). Further down the development pathway, Spurs Web report Tottenham have joined Real Madrid in a chase involving several clubs for a 15-year-old German midfield prodigy (Spurs Web), though another report says Spurs and Arsenal have both been stopped in their tracks in a January pursuit of winger Nicolo Tresoldi (Spurs Web). There was also news out of Old Trafford, with Spurs Web suggesting Tottenham's recruitment staff will be keeping tabs on Sunday's game there following the latest Eli Junior Kroupi update (Spurs Web).
In loan and squad news, Football.London's round-up includes a first senior appearance for a Tottenham wonderkid out on loan, alongside some struggles for Radu Dragusin and praise for Jamie Donley (Football.London). Spurs Web report that young defender Luca Gunter has been recalled from his loan at Boreham Wood after losing his place in the side (Spurs Web). Former Spurs defender Luka Vuskovic has also spoken out about his departure from the club, saying he does not know why Tottenham did not want to keep him before his move to Brighton (Spurs Web).
Away from the pitch, Spurs Web report a leak suggesting Tottenham's 2027/28 third kit will feature a black design and possibly a tweaked badge (Spurs Web). And pundit Gus Poyet has given his view on the pressure facing De Zerbi, outlining the lowest position he believes Tottenham should finish this season (Spurs Web).
This round-up is written with the help of AI, using only the day's headlines from the publishers credited above. Each point links to the original report — tap the source name to read it in full.