Reports from Italy claim that Tottenham had a £30m bid for Fiorentina's Giovanni Simeone rejected during the summer, before Spurs ended up finishing the window without signing a single first team player.
According to Tuttosport, Tottenham were heavily interested in the Argentine striker, who signed from Genoa one year ago, but Fiorentina bosses were in no mood to depart with the 23-year-old.
Instead they confidently rebuffed the advances from the Premier League side with the intention of holding onto their star striker until January at the earliest.
Signing off the back of a prolific spell with Genoa, Simeone scored 14 goals in 38 Serie A appearances last term, sparking rumours of interest from Spurs, who reportedly remain interested in the forward as a strong alternative to Harry Kane.
The report also claims that Atletico Madrid, managed by Simeone's dad Diego, are interested in the forward, and the player is keen to play under his dad at some point in the future.
The younger Simeone has done his prospects no harm this season either, scoring and earning the man of the match reward in a 6-1 victory over Chievo Verona.
He wasn't the only target Spurs failed to acquire this summer, as they became the first side in the history of the summer transfer window not to sign a single player.
Their lack of transfer business hasn't exactly had a negative impact on their football, however, as they have started the Premier League season with three wins out of three - most recently hammering Manchester United 3-0 at Old Trafford.