During his first season in Kansas City, Green struggled despite the presence of tight end Tony Gonzalez, and running back Priest Holmes. He threw for 3,783 yards and 17 touchdowns, but also threw 24 interceptions. Green showed marked improvement in 2002, throwing 26 touchdowns to only 13 interceptions as the Chiefs went 8-8. Also notable, Green tied the record for longest career pass play in NFL history (99 yards) on December 22, 2002, on a pass to Marc Boerigter in a game against the San Diego Chargers. In 2003, Green had his breakout year, throwing for 4,039 yards, 24 touchdowns, and 12 interceptions. He led the Chiefs to a 13–3 record and a first-round bye in the playoffs. However, in the divisional playoff game, they lost a 38–31 shootout to Peyton Manning and the Indianapolis Colts. The game was notable for there being no punts by either team, a first in NFL playoff history. Green was elected to his first Pro Bowl that year. The next season, the Chiefs went 7–9 as Priest Holmes suffered a knee injury in their eighth game against the Tampa Bay Buccaneers in Tampa, Florida and missed the rest of the regular season. At the time, he was leading the league in both rushing and scoring. However, Green still had a stellar year, passing for 4,591 yards, 27 touchdowns, and 17 interceptions. His passing total for 2004 was second only to Minnesota's Daunte Culpepper.