On May 2, 1999, at the age of 38, Elway announced his retirement from professional football. Elway is regarded as one of the top quarterbacks ever to play the game. He has one of the best winning percentages in league history (148–82–1), and was tied for the second-most Pro Bowl selections for a quarterback (nine) at the time of his retirement. Elway played in 22 postseason games with the Broncos, 21 as a starter, and led the team to victory in 14 of them. In those games he threw for 4,964 yards and 27 touchdowns, with 21 interceptions, while also rushing for 461 yards and 6 more scores. He is currently 9th all time in passing yards , 10th in passes completed, , and 12th in passing touchdowns . His four total rushing touchdowns in his Super Bowl games are the most ever by a quarterback. He is also the second player ever to score a rushing touchdown in four different Super Bowls (running back Thurman Thomas was the first).
On September 13, 1999, Elway's number 7 jersey was retired by the Denver Broncos during halftime of a Monday Night game against the Miami Dolphins; that same night he was inducted into the Denver Broncos Ring of Fame. (Craig Morton, his direct predecessor in Denver, also wore number 7 and is in the Ring of Fame alongside Elway). He was the first Broncos player to have the five-year waiting period waived. Also in 1999 he was inducted into the Colorado Sports Hall of Fame.
Also in 1999, Elway was ranked number 16 on The Sporting News' list of the 100 Greatest Football Players, the only player to have spent the majority of his career with the Broncos to make the list (Willie Brown, who began his career with the Broncos but spent more of it with the Oakland Raiders, also made the list). In 2005, TSN published another special feature honoring the 50 Greatest Quarterbacks. Elway was ranked third behind Johnny Unitas and Joe Montana.