Winks was only 12 when Modric joined Spurs in 2008 but, nine years later, the pair went head-to-head on the biggest stage - in the Champions League at the Bernabeu.
Tottenham took a valuable point away from the Spanish capital, and the performance of Winks was one of the most eye-catching among a host of established names.
The 21-year-old has only five Premier League starts in his career but he was aggressive and brave in possession, seemingly unfazed by the prospect of taking on two of the world's finest midfielders in Modric and Toni Kroos.
"When I was coming through the academy at a young age he was someone I always used to watch at White Hart Lane," Winks said. "I still admire him to this day - he's a fantastic, world-class player. To play against him was special.
"Him and Kroos, they are two fantastic, world-class players, players I look up to, so when you go on the pitch with them it's easy to get a little bit daunted by it.
"But I try to take all that away from it, treat it like any normal game and just go for them as I would any other player. Being on the pitch with them you realize their quality and just how good they are."