Robertson, Gallas and Sheringham: How Spurs' free agent signings fared at the club

Tottenham have shattered their transfer record twice in the same summer, spending a combined £185 million on Sandro Tonali and Mateus Fernandes as manager Roberto De Zerbi attempts to rebuild after a difficult 2025/26 campaign. Alongside those headline deals, Spurs have also moved quietly in the free agent market, securing Andy Robertson, Marcos Senesi and Martin Dubravka on no-fee deals.

That blend of big spending and cost-free acquisitions is nothing new at Spurs. The club has a track record of extracting real value from players arriving without a transfer fee, with varying degrees of success.

Teddy Sheringham

Sheringham’s first spell at Spurs was not a free transfer — he arrived from Nottingham Forest for around £2.1 million in 1992 and developed into one of the Premier League’s most reliable forwards during his time in north London. A lack of silverware, however, prompted a £3.5 million move to Manchester United in 1997.

At Old Trafford, Sheringham was part of the side that completed the Treble in 1999, scoring and assisting in the Champions League final comeback against Bayern Munich. After further success at United, he returned to Spurs on a free transfer in 2001, eventually accumulating 277 appearances and 125 goals across both spells. He was inducted into the club’s Hall of Fame in 2008, the same year he retired.

William Gallas

Gallas is one of the more complex figures in recent Premier League history, having represented Chelsea, Arsenal and Tottenham in succession. He joined Chelsea from Marseille for £6.2 million in 2001 before moving to Arsenal in 2006, where he was eventually handed the captaincy — a role he later lost to Cesc Fabregas amid reported internal tensions.

When his Arsenal contract expired in 2010, Gallas crossed north London to join Spurs on a free transfer, adding experience and Premier League pedigree to the backline. His stint at White Hart Lane gave the club a former Gunners captain at no cost, a piece of business that raised eyebrows but made sound financial sense.

Andy Robertson

Robertson arrives at Spurs this summer as the most decorated of the three, having won the Premier League, Champions League, FA Cup and League Cup during a trophy-laden spell at Liverpool. The Scotland captain’s contract at Anfield ran its course, allowing De Zerbi to add an experienced international left-back without a transfer fee.

At 31, Robertson brings leadership and top-level experience to a squad in transition. Whether he can replicate the consistency he showed at Liverpool remains to be seen, but the financial logic of the signing is straightforward — elite pedigree, zero outlay.

With further transfer activity reportedly in the pipeline, De Zerbi appears intent on combining marquee signings with opportunistic free agent deals as Spurs look to return to contention.