The Spurs Legends team slipped to a 3-2 defeat against a determined Southgate County side at Potters Bar Town's ground on Sunday.
Two early goals saw Southgate seize an early advantage, but the ex-White Hart Lane stars soon got themselves back into the contest with goals from James Bunn and Trevor Wilkinson.
Joining regular stars Tony Galvin, Mark Falco and Stuart Nethercott in the starting line-up was Paul Moran and David Kerslake among others.
Ken Middleton put Southgate into a fifth minute lead before Martin Payne made it 2-0 on eight minutes.
Spurs soon got themselves into gear and Bunn's excellent low strike from 25 yards found the bottom corner of the net on 11 minutes.
Moran's cross from the right was met by Wilkinson, who controlled the ball before firing home the equaliser from 10 yards out with 20 minutes on the watch.
Both sides had chances before the half-time interval arrived but, even with the introduction of Les Boughey from the bench 10 minutes into the second half, Spurs were unable to find a breakthrough and Southgate clinched the winner through Ben Stones on 65 minutes.
Spurs Legends: Tony Tillbrook, Stuart Nethercott, Tony Galvin, Mark Falco, Andy Edmunds, David Kerslake, Paul Moran, James Bunn, Steve Smart, Micky Jarrett, Trevor Wilkinson. Sub: Les Boughey.