The 34-year-old Figueroa, who donned the W Connection shirt between 2001-2005, after brief spells with Doc’s Khelwalaas and San Juan Jabloteh, was a free agent before being recalled by Connection.
The move by Connection came after a reported verbal bust-up between first-choice goalie and ex-captain Jan-Michael Williams and technical director/coach Stuart Charles-Fevrier.
The 28-year-old Williams was axed by the club as a result and Figueroa will be challenging Aquelius Sylvester and Brazilian Murilo Da Costa for a regular spot between the uprights.
Figueroa was one of the most valuable acquisitions by Joe Public between 2006-2009 winning a historic five titles with the Lions before joining Ma Pau SC for the 2010-2011 followed by a premature exit and his return to Colombia.
Williams, who joined Connection team in 2003 and had spells in Europe with Belgian football club White Star Woluwé (2007-2008) and Hungarian club Ferencvárosi TC (2008-2009) before returning to Trinidad, is hopeful of returning abroad to play professionally.
In related news, Connection also made another signing in St Lucian midfielder Tresmain Paul of Pakis FC.
Connection owner David John-Williams said that his coach scouted the 21-year-old during the Christmas vacation in St Lucia — home of Charles-Fevrier and assistant coach Earl Jean.