Tottenham transfer news: Spurs have been handed an unexpected second chance to sign Union Saint-Gilloise winger Anan Khalaili. The 21-year-old looked destined for Serie A earlier this summer. Inter Milan had agreed on a €25m package, leaving Spurs to look elsewhere. But the entire deal collapsed at the eleventh hour. Italy’s strict CONI medical assessments flagged issues, forcing the Italian champions to walk away from the table. That failed medical changes the game for Peter Carrington and Roberto de Zerbi.
Tottenham transfer news: Anan Khalaili back on radar
The Nerazzurri pulled out after those rigorous Italian health checks put the brakes on a five-year contract. It is a massive blow for the player. However, Italian sports regulations are notoriously stringent regarding cardiopulmonary standards, often red-flagging issues that medical teams in the Premier League clear without a second thought.
Spurs had backed off initially. They wanted to avoid a messy bidding war with the Milan executives, especially when the Israeli international made it clear he preferred the San Siro. Now, he is stuck back in Belgium. The north London club have a clear run at him if they choose to strike.
Khalaili is coming off a massive workload for Union Saint-Gilloise. He racked up 3,099 minutes across 38 league games in the 2025/26 campaign. That is serious mileage for a young wide player. He managed three goals and five assists in domestic competition, but his European displays really attracted attention. A brilliant brace against Marseille in the Champions League group stage proved he can deliver on the big stage. De Zerbi needs depth out wide. High-intensity directness is non-negotiable in this current system, and Khalaili fits the profile perfectly.
VF’s opinion: What happens next for Spurs
Union Saint-Gilloise wanted around €23m up front before the Italian move fell apart. Whether that price tag drops now remains the big question. Spurs can test their resolve. Everything depends on the Tottenham medical staff doing their own homework. If they check the fitness reports and find no lasting issues, this is a huge market opportunity. A top-tier talent is suddenly up for grabs with almost zero competition. Spurs just need to decide if they want to hit the accelerator.