Tottenham Hotspur, speaking overall, did enjoy a productive summer 2025 transfer window. They made Mathys Tel's loan from Bayern Munich permanent, added Joao Palhinha on loan from the Bavarian giants, bagged striker Randal Kolo Muani on loan on transfer deadline day from Champions League winners PSG (though he played for Juventus during that time), and had both Xavi Simon and Mohammed Kudus as crown jewel signings of the period.
The thing is, though, Tottenham's list of transfers they missed out on, once again, was even better than the players they signed. They failed to bring in Savinho near the end of the window from Manchester City, and they also lost out on marquee Man City signing Rayan Cherki at the beginning of the window.
Both Eberechi Eze and Christian Norgaard rejected Spurs for rivals Arsenal. Yoane Wissa spurned Thomas Frank to sign up with Newcastle United. Bryan Mbeumo did the same, penning a contract with Europa League Final rivals Manchester United. And Morgan Gibbs-White pulled the rug out from under Tottenham by signing a contract extension with Nottingham Forest after owner Evangelos Marinakis threw a tantrum when Spurs activated his hidden release clause.
Tottenham's regret will haunt them
But if you ask many Spurs fans, the transfer they regret not making the most was Morgan Rogers, who would have completed their ailing attack perfectly as a proven source of progression, creation, and even goal scoring from that left flank, as well as playing other positions.
Well, Rogers only made the Tottenham transfer regret even stronger on Sunday with a game winning performance against Manchester United - the same team Spurs could not beat this season. Aston Villa won 2-1 behind Rogers's two goals, and his first goal was completely out of nowhere with a beautiful touch, dribble around Leny Yoro, and a curled finished that left the Man United keeper rooted to the spot. Arjen Robben would be proud.
Rogers did have an awful start to the season, but he has redeemed himself since, and this one performance against Manchester United both epitomizes his game changing ability and was far beyond anything any Spurs attacker (aside from Kolo Muani against PSG) has produced in an individual display this season.
Tottenham are going to be back in for Savinho this January transfer window after Antoine Semenyo apparently turned them down, but you have to wonder if Spurs fans will try to push the club to finally make a real effort for Rogers.