Caguioa played collegiate basketball at Glendale Community College. He was named to the First Team All-Western State Conference after the 1999–2000 season.
In 2001, Caguioa was drafted by the Barangay Ginebra Kings as the third overall pick. Expectations were not high as Caguioa started as a role player and backup for superstar Vergel Meneses. However, after showing strong performances and helping to lead the Kings to the 2001 All-Filipino Cup Finals, he became very popular. With his crossovers, drives to the basket, and penchant for making clutch plays, Caguioa earned the respect and admiration of the Filipino basketball fans. His exciting brand of play earned him the moniker "The Spark." At the end of his first season, Caguioa was the third Ginebra player, after Dondon Ampalayo in 1986 and Marlou Aquino in 1996, to win the Rookie of the Year award. For the 2011–2012 season, he won the Most Valuable Player award.
"The Fast and The Furious"
In the 2004–05 season, Caguioa, along with his backcourt partner Jayjay Helterbrand, formed a strong tandem, which was dubbed as "The Fast and The Furious". Their play enabled Ginebra to win back-to-back championships. Caguioa also set his then career high for points in a single game during that season, scoring 43 points in Game 4 of the Philippine Cup Finals against the Talk 'N Text Phone Pals. In the 2006 Philippine Cup, Caguioa earned "Player of the Week" honors three times. He led the league in scoring at 24 points per game, and broke his previous career high for points in a single game, scoring 45 points in a losing effort against Red Bull in the quarterfinals. He became the first guard to finish a single season as the league's leading scorer since Allan Caidic in 1995. In the 2007 Philippine Cup, Caguioa averaged 24.7 points per game in the 23 games he played. He also led the league in statistical points for the Best Player of the Conference Award. Caguioa piloted Ginebra to their seventh championship in franchise history by besting the San Miguel Beermen in a best-of-seven finals. During their series against Talk 'N Text in the semifinals, Caguioa scored 34, 31, 26, 35, and 31 points in the five games. Caguioa won the 2007 PBA Best Player of the Conference. Caguioa again helped his team during the 2008 PBA Fiesta Conference, culminating in the team's eighth championship. He also led the league in scoring. In the 2008–09 season, Caguioa failed to suit up for Kings due to his therapy in the United States for tendinitis on both knees. Caguioa received the MVP award and back to back Best Player of the Conference awards in 2011 and 2012. In October 5, 2018 against NLEX Road Warriors, Caguioa scores 16 points to join the PBA 10,000 points club.
International career
Caguioa was named in the RP Training Pool for future international competitions. He participated in several exhibition games against the Iranian National Team and the NBL's Sydney Kings in mid-2005, where he impressed the latter team's coach by scoring 27 points. He has also played in the 2005 FIBA Asia Champions Cup held in the Philippines, in which his team finished fifth. He averaged 19.8 points and 3.4 rebounds per game in that tournament. However, Caguioa was eventually dropped from the team. National mentor Chot Reyes claimed that Caguioa had failed to appear for several practice sessions. In 2007, he joined the national team that won the SEABA Championship with a perfect record and finished ninth place with a record of 5–2 in the 2007 FIBA Asia Championship.