1999 - Played first event of career at ITF/Tallinn-EST (in hometown).
2000 - In only event of season, won ITF/Tallinn-EST singles title.
2001 - Successfully defended ITF/Tallinn-EST singles title; played first Tour main draw at Vienna, falling 1r (as qualifier, l. to A.Huber).
2002 - Reached 2r twice; fell 1r once and in Tour qualifying six times (incl.
Australian Open and
US Open); continued to play on ITF Circuit.
2003 - Fell in Tour qualifying twice (incl.
US Open); won two singles titles and one doubles title on ITF Circuit.
2004 - Fell in Tour qualifying four times (incl.
Australian Open,
Roland Garros); played first Olympics (l. 1r); won one singles title on ITF Circuit; suffered right knee injury after Olympics and did not play again until February 2005.
2005 - SF at Kolkata (l. to Myskina); fell 1r once and in Tour qualifying once (
US Open); won one singles title on ITF Circuit; made Top 100 debut on December 19 (rose from No.117 to No.98).
2006 - First Top season; runner-up at Hasselt (l. to Clijsters); was first Estonian ever to reach a Tour singles final; SF at Prague (l. to Peer); reached 3r once (
US Open) and 2r five times (incl.
Roland Garros); fell 1r eight times (incl.
Wimbledon) and in Tour qualifying five times (incl.
Australian Open).
2007 - Second Top 100 season; SF at Bad Gastein (l. to Schiavone); QF at Barcelona; reached 3r once and 2r six times (incl.
Australian Open,
Wimbledon); fell 1r eight times (incl. other two majors) and in Tour qualifying five times; made Top 50 debut on April 2 (after Miami; rose from No.56 to No.50); won one doubles title on ITF Circuit; dipped to No.75 by year's end after withdrawing from Beijing, Guangzhou and Tokyo [Japan Open] w/right shoulder injury.
2008 - First Top 30 season; first Estonian ever to reach a Grand Slam QF at
Roland Garros (l. to Kuznetsova); runner-up at Tokyo [Japan Open] (l. to Wozniacki in final); SF twice, at Acapulco (l. to Pennetta) and Seoul (l. to Kirilenko); QF three more times, at Sydney (l. to Henin), Viña del Mar (l. to Pennetta) and Tokyo [Pan Pacific] (l. to Safina); reached 4r once, 3r once (Olympics) and 2r five times (incl.
US Open); fell 1r seven times (incl.
Australian Open,
Wimbledon); blew past previous career-high No.40 on June 9 (after
Roland Garros; rose from No.49 to No.34) and peaked at No.27 on October 27 (stayed there until November 10 year-end rankings); withdrew from Amelia Island w/illness, from Istanbul w/fatigue, from Barcelona w/hip injury, from Bad Gastein and Portoroz w/shin splints and from Stockholm w/recovery from appendix operation.
2009 - Fourth straight Top 100 season; went 15-10 in first 10 events, reaching SF at Dubai (as No.16 seed, d. No.3 seed Jankovic en route; l. to Razzano), two QF at Marbella (as No.3 seed, l. to No.7 seed Cirstea 75 third set) and Rome (as No.16 seed, l. to No.6 seed Azarenka), three 3r at
Australian Open (as No.25 seed, l. to No.3 seed Safina), Indian Wells (as No.18 seed, l. to No.9 seed Wozniacki in 3s) and Miami (as No.21 seed, l. to No.10 seed A.Radwanska) and two 2r at Sydney (l. to No.5 seed Kuznetsova 76 third set) and Paris [Indoors] (d. No.7 seed Medina Garrigues in 1r; l. to qualifier Loit in 3s); fell just twice in first 10 events; made Top 20 debut on February 23 (after Dubai; rose from No.24 to No.20 - first Estonian ever to crack Top 20) and peaked at No.18 on May 25; suffered 11 straight 1r losses to finish season, beginning with Madrid (as No.16 seed, ret. vs. Safarova w/left hip injury) and also including
Roland Garros (as No.19 seed, l. to qualifier Shvedova in 3s),
Wimbledon (as No.25 seed, l. to Suárez Navarro in 3s) and
US Open (as No.25 seed, l. to qualifier Chang); was No.61 on November 9 year-end rankings; withdrew from Acapulco w/viral illness, from Birmingham and Eastbourne w/left knee injury and from Linz w/left ankle injury.