Given that his choice comes from his second stint at the Lane, it is of little surprise that the departing skipper spotlights a certain home game and a resounding win that bucked an unwanted trend over recent years.
"I think the highlight would probably be beating Chelsea in the semi-final of the cup," smiled Teddy as he recalled the 5-1 triumph that followed a 2-1 defeat at Stamford Bridge.
"It was one of those nights. We hadn't beaten Chelsea for so long and were losing 2-1 already.
"The boys were so fired up on that night and everything went according to plan. To beat them in a second leg semi to make sure you go to final made it a great night.
"It's one that will live with me for a long time because it was so enjoyable."
Teddy Sheringham has identified his personal high point from his two spells at the club.