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, with Cristiano Ronaldo's penalty cancelling out an own goal by Raphael Varane, but Winks' performance 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. And for Winks, facing Modric was particularly special.
"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 realise their quality and just how good they are."
Harry Kane could have won it for Tottenham when his finish was saved by Keylor Navas late on but the visitors had Hugo Lloris to thank after he made a string of superb saves.
The pick of the bunch saw Lloris deny Karim Benzema from point-blank range, the striker's header somehow kept out by his compatriot's legs.
"He is world class, one of the best keepers in the world," Winks said.
"He kept us in the game with some fantastic saves. The Benzema chance, the way he saved it I will never know.
"He makes saves not many people can which is why he's up there with the best keepers in the world."
Winks' display against such testing opposition will surely not have gone unnoticed by Gareth Southgate, who called the youngster up to the England squad for the first time last month.
Tottenham defender Danny Rose believes Winks was Spurs' star player.
"I'm over the moon with the team, in particular with Harry Winks," Rose said.
"He was probably our best player. It's nothing more than he deserves, he's done extremely well over the last few years. We're all proud of each other, the manager is proud of us."