Kaia Kanepi failed to qualify at the last hurdle for the WTA500 tournament in Adelaide, Australia, after losing to Sorana Cirstea of Romania in three sets, 6:2, 4:6, 7:5.
Kanepi, ranked 32nd in the world, beat Hungary's Anna Bondar in straight sets in the preceding round, putting her one win away from qualifying for the main draw at Adelaide.
Cirstea (WTA 45th), had overcome Camilla Giorgi (Italy, WTA 66th) in the previous round.
Kanepi and Cirstea had last met back in 2014 in New Haven, with Kanepi emerging the victor that time.
In the first set, which lasted 36 minutes, Kanepi had a 41 percent first service success rate and, while she was presented with three break points, Cirstea, a former French Open quarter finalist, fended all these off and took the set 6:2.
In the second set, the roles were reversed as Kanepi herself was able to save three breakpoints which Cirstea reached; the Estonian broke on the fifth attempt, in the ninth game of the set, and went on to win the set 6:4.
In the decider, Kanepi went 5:3 up, yet failed to win another game, as Cirstea strung together four games to take the set 7:5, and with it the match, and qualification to the Adelaide tournament proper.
The entire encounter lasted two hours and nine minutes.
Kanepi committed six double faults and had a first service success rate of 49 percent.
For Cirstea, the figures were two, and 69 percent, respectively.
The Romanian won 54 percent of all points played.
Top Estonian player Anett Kontaveit (WTA 17th) is to face Paula Badosa (Spain, WTA 13th) in the opening round of the Adelaide main event.
The tournament is one of several, including two to have taken place in Adelaide, ahead of the Australian Open starting in Melbourne on January 16, the first grand slam competition of 2023.
Editor's note: This article corrects several factual errors in an earlier version.
Editor: Andrew Whyte, Janno Joala