As a teenager, Caulker showed talent in athletics and chose to pursue football with his local club, Hounslow Borough. He initially played as a central midfielder but moved to central defence after a coach’s advice. At 15 years old, he played one match as a centre-back for Hounslow and received trial offers from seven clubs, including Tottenham Hotspur and Chelsea.

Caulker joined the Tottenham Hotspur youth team, starting with the Under-18s in the 2007–08 season. In the 2008–09 season, he made 31 appearances, scored one goal, and captained the team. He also played five matches for the reserve team. His strong performance led him to sign his first professional contract with Tottenham in July 2009.

After loan spells at Yeovil Town, Bristol City, and Swansea City, he returned to the London club on July 5, 2012, and signed a new four-year contract with Tottenham Hotspur, lasting until the summer of 2016.

In discussing the players at Tottenham, he highlighted Gareth Bale and Luka Modric.

The best player I’ve played with: is Gareth Bale. In the 2012-2013 season, Gareth was amazing. He kept us in the top-four race with his last-minute goals. He is very humble and a great professional.

The best player I’ve trained with: “Luka Modrić. I was 16 when I joined the first team for a training session; I was nervous. Luka walked out to training calmly. He is a fantastic player. He can see passes quickly, and his balls have perfect weight.

On training with world-class players – I have been lucky to play and train with many of the world’s best players: Steven Gerrard, Phil Coutinho, Ryan Giggs, Mesut Özil, Wayne Rooney, Harry Kane, Virgil van Dijk, Rio Ferdinand, Sadio Mané, and Arda Güler, among others.

They all have different skills, but they share one important thing: discipline. Rio was always first in line for warm-ups. Gareth took care of his body to recover well. Ryan did yoga even at 40, and Harry always practised his finishing.

Most did not talk much in the dressing room; they let their football speak for them. I don’t think there is one way to be great, but from my experience, without discipline, few players stay at the top for long—myself included.”