This refers to a football team in Northern London that let go of their best player Harry Kane and haven't won a trophy since the 1960x
Person 1 - What does trophyless mean?
Person 2 - oh are you talking about Tottenham ?
This is a phrase commonly used to yab or insult other people, it is also used for a comeback for literally anything!
Dude 1: You are so stupid
Dude 2: like ur mom
Dude1: You fail in school
Dude 2: like ur mom
Dude 1: who was eating that?
Dude 2: ur mom xd