Pete Sampras, Andre Agassi, and Michael Chang were among the top young players in the world in the late 1980s and early 1990s. They were all born within a few years of one another in the early 1970s. At Roland Garros in 1989, Chang, only 17 years old, won his first and only Major title. Agassi then seized the initiative in 1990 to overtake Chang and Sampras.
Three teenage Americans were among the favorites at the Canada Open at the end of July in Toronto. Due to their placement in the same half of the draw, only one could proceed to the title match. Chang defeated world no. 1 in the quarterfinal.
Agassi 7-5 in the third set to advance to the championship round and face Sampras. It was their fourth encounter on the Tour, and Michael defeated Pete 3-6, 7-6, 7-5 in more than two hours to go to the opening Masters 1000 final.
Sampras scored two more points than Chang, and they each made two breaks to stay even. Pete had 20 more unforced errors than Michael, which cost him ground. Pete had more winners and forced more errors to establish the advantage.
Pete Sampras was defeated by Michael Chang in the 1990 Canada Open semifinal.
In the quickest rallies, Sampras prevailed. In the longer exchanges, Chang overcame the gap to take first place and keep his title chances alive.
In the second game of the match, Michael held off two break chances, one at 1-2 and the other with wins. In the sixth game, Pete finally caught a break to increase his lead and held at 15 a few minutes later to edge ahead 5-2.
Before Sampras held at 15 in the following game to win the opening set in ease, Chang saved two set points in the eighth game. In set two, Michael improved, and they both played effectively to a score of 4-4. After two deuces, the younger American won the ninth game to force a tie break and end the set.
When his opponent sprayed a forehand error, Michael stayed focused and won 7-5. In the second game of the third set, Chang was broken for the second and final time. She then missed three break opportunities in the following game, falling behind 3-0.
After an outstanding defensive performance, Michael recovered a break at 1-3 and held at love to tie the game at 3-3. Pete, who was losing ground at the time, saved a break point in the following situation, and they remained competitive until 5-5.
Sampras made a backhand error in the eleventh game to lose a break and give the opponent the lead, which proved to be the turning point of the entire match. Chang secured the victory and defeated a fellow countryman for the fourth time in a row by holding after two at 6-5.