The storied coaching rivalry between Chot Reyes and Yeng Guiao, a fixture in Philippine basketball, stretches back more than three decades, commencing in 1993 when Reyes first took the helm at Purefoods against Guiao, who was already coaching within the RFM franchise in the PBA. Their enduring competition is set to add another chapter as they face off in the PBA playoffs for the third consecutive semifinals, and fourth overall in the 49th Season Philippine Cup.

Statistical data from PBA statistics chief Fidel Mangonon reveals the extensive history of their encounters. Prior to Game 1 of the 49th Season Philippine Cup semifinals between Rain or Shine and TNT, Reyes and Guiao had already competed in 104 games across elimination rounds, playoffs, and finals. In this long-standing head-to-head, Reyes holds a significant lead with 62 wins, while Guiao has secured 42 victories.

Throughout their careers, both coaches have helmed a multitude of teams, adding layers to their rivalry. Reyes' coaching stints include Purefoods, Coke, Sta. Lucia, and various iterations of the RFM franchise like Pop Cola/Swift/Sunkist, and more recently, TNT. Guiao's journey has seen him lead teams such as Red Bull, Burger King, Air21, NLEX, and Rain or Shine.

Beyond the PBA sidelines, their paths have also converged and diverged. Reyes briefly served as the executive director of the Metropolitan Basketball Association (MBA), while Guiao was a commissioner for the Philippine Basketball League (PBL) in the late 1990s. Despite these detours, both eventually returned to the PBA in 2000, with Guiao coaching the expansion team Red Bull and Reyes taking over Pop Cola, coincidentally from the RFM franchise where Guiao began his PBA coaching career.

Their careers also share notable similarities. Both coaches have had the distinction of leading the Gilas Pilipinas national team. Notably, Guiao succeeded Reyes as Gilas coach in 2018 after Reyes stepped down following the infamous brawl involving the Philippines and Australia in the FIBA Basketball World Cup Asian qualifiers. Furthermore, both were at one point part of the MVP Group conglomerate, with Guiao coaching NLEX from 2016 to 2022.

Despite the frequency of their competitive meetings, the Reyes-Guiao coaching match-up has surprisingly only featured one finals showdown. This sole championship clash occurred in the 1993 Commissioner's Cup finals, where Guiao, leading Swift, emerged victorious against Reyes' Purefoods squad. This limited number of finals encounters has arguably made their otherwise sustained and significant rivalry somewhat underrated, especially when contrasted with Reyes' more frequent finals battles against Barangay Ginebra coach Tim Cone, whom he has faced eight times in championship series. Guiao's Rain or Shine teams in the 2010s, when reaching the finals against TNT, typically faced Norman Black or Jong Uichico, often ending on the losing side.

However, with the recent strong performances of both TNT and Rain or Shine in current conferences, there is growing anticipation among basketball observers that the Reyes-Guiao rivalry may soon culminate in a long-awaited PBA finals confrontation, adding a dramatic new chapter to their storied and intertwined careers.