The former Premier League powerhouse, 38, played for Spurs' rivals West Ham for four years between 2003 and 2007, but that rivalry appears to have been thrown out of the window in Harewood's eyes.
Joining the east Londoners in 2003 from Nottingham Forest, Harewood went on to make 170 league and cup appearances for West Ham in four seasons, scoring 56 goals and helping the club gain promotion to the Premier League in 2005.
Posting a picture of both right-back Trippier and playmaker Alli's shirts on his personal Instagram account, Harewood described the Spurs duo's tops as a "nice little delivery" before thanking the Spurs stars.
West Ham and Spurs have already gone toe to toe twice this season, with Spurs winning in the league 3-2 thanks to a brace from Harry Kane and Christian Eriksen strike, but West Ham exacted their revenge in the Carabao Cup with a 3-2 win of their own.
Leaving West Ham in 2007, Harewood became somewhat of a journeyman, playing for 11 clubs in nine years including the likes of Aston Villa, Newcastle United and Hartlepool, as well as Chinese outfit Ghangzhou R&F.