Juniors

Pless had an excellent junior career, winning the 1999 Australian Open Boys' Singles (defeated Mikhail Youzhny), and reaching the Boys' final at both Wimbledon (lost to Jürgen Melzer), and the US Open (lost to Jarkko Nieminen) the same year. He finished 1999 as the No. 1 ranked junior player in the world.^[1]

Pro tour

He turned professional in 1999, and on 28 January 2002, Kristian Pless reached his career-high ATP singles ranking of World No. 65. He has won tournaments at the Futures and Challenger levels, and has reached three semifinals on the ATP Tour. He suffered a serious shoulder injury in 2003, which after multiple surgery kept him out of competition for almost a year.

After returning from injury in 2004, he had dropped in the rankings to World No. 846 on 24 May. Subsequently, he has gradually climbed the rankings, and after successful performances at the Challenger level in autumn 2006, he entered the Top 100 again. In January 2007, he continued his good performances as he defeated World No. 8 David Nalbandian in three sets in the first round of Chennai Open. This was Pless' first win against a Top-10 ranked player.

In 2007 he also managed to take a set from tennis legend Roger Federer at their meeting in Dubai, but eventually Federer won the tie 7–6⁽²⁾, 3–6, 6–3. It was first set Federer had lost that year after he had won the Australian Open without losing a single set.

In 2008 he reached two Challenger finals (in Izmir, Turkey and Rimouski, Canada), but ended the year outside of Top 100. 2009 was his last year on tour.^[2]

Singles: 3 (1 title, 2 runner-ups)

Result	Year	Tournament	Surface	Opponent	Score
Win	1999	Australian Open	Hard	Mikhail Youzhny	6–4, 6–3
Loss	1999	Wimbledon	Grass	Jürgen Melzer	6–7, 3–6
Loss	1999	US Open	Hard	Jarkko Nieminen	7–6, 3–6, 4–6

Doubles: 2 (1 title, 1 runner-up)

Result	Year	Tournament	Surface	Partnet	Opponents	Score
Win	1999	Australian Open	Hard	Jürgen Melzer	Ladislav Chramosta Michal Navrátil	6–7, 6–3, 6–0
Loss	1999	French Open	Clay	Olivier Rochus	Irakli Labadze Lovro Zovko	1–6, 6–7

Singles: 20 (7–13)

Result	W–L	Date	Tournament	Tier	Surface	Opponent	Score
Loss	0–1	Apr 1999	New Zealand F3, Christchurch	Futures	Hard	Louis Vosloo	4–6, 3–6
Win	1–1	May 2000	Austria F3, Schwaz	Futures	Clay	Scott Barron	6–3, 7–5
Win	2–1	Jun 2000	Ireland F1, Dublin	Futures	Carpet	Grant Doyle	6–3, 6–7(5–7), 6–1
Win	3–1	Aug 2000	Hungary F6, Budapest	Futures	Clay	Alexander Peya	7–5, 6–3
Loss	3–2	Feb 2001	Hull, United Kingdom	Challenger	Carpet	Michael Kohlmann	7–5, 6–7(3–7), 6–7(5–7)
Win	4–2	May 2001	Edinburgh, United Kingdom	Challenger	Clay	Gorka Fraile	6–3, 6–3
Loss	4–3	Jun 2001	Furth, Germany	Challenger	Clay	Germán Puentes	4–6, 3–6
Win	5–3	Dec 2001	Rio de Janeiro, Brazil	Challenger	Hard	Ricardo Mello	6–1, 6–1
Loss	5–4	Jun 2004	Poland F3, Warsaw	Futures	Clay	Dušan Karol	3–6, 4–6
Loss	5–5	Aug 2005	Belo Horizonte, Brazil	Challenger	Hard	John Paul Fruttero	6–7(4–7), 6–7(6–8)
Loss	5–6	Oct 2005	Southampton, United Kingdom	Challenger	Hard	Jérôme Haehnel	2–6, 3–6
Loss	5–7	Jul 2006	Dublin, Ireland	Challenger	Carpet	Mischa Zverev	5–7, 6–7(6–8)
Loss	5–8	Oct 2006	Nottingham, United Kingdom	Challenger	Hard	Alexander Waske	4–6, 3–6
Win	6–8	Nov 2006	Rimouski, Canada	Challenger	Carpet	Lu Yen-hsun	6–4, 7–6(7–5)
Loss	6–9	Nov 2006	Nashville, United States	Challenger	Hard	Robin Haase	6–7(9–11), 3–6
Win	7–9	Apr 2007	Saint-Brieuc, France	Challenger	Clay	Farrukh Dustov	6–3, 6–1
Loss	7–10	Sep 2007	Grenoble, France	Challenger	Hard	Nicolás Lapentti	3–6, 5–7
Loss	7–11	Mar 2008	Cherbourg, France	Challenger	Hard	Thierry Ascione	5–7, 6–7(5–7)
Loss	7–12	Jun 2008	Izmir, Turkey	Challenger	Hard	Gilles Müller	5–7, 3–6
Loss	7–13	Nov 2008	Rimouski, Canada	Challenger	Hard	Ryan Sweeting	4–6, 6–7(3–7)

Doubles: 7 (4–3)

Result	W–L	Date	Tournament	Tier	Surface	Partner	Opponents	Score
Loss	0–1	Apr 1999	New Zealand F3, Christchurch	Futures	Hard	Mark Nielsen	Wynn Criswell Shaun Rudman	2–6, 6–2, 1–6
Win	1–1	Dec 1999	Lucknow, India	Challenger	Grass	Paradorn Srichaphan	Martin Lee Jamie Delgado	5–7, 6–3, 7–5
Loss	1–2	Jun 2000	Ireland F1, Dublin	Futures	Carpet	Jarkko Nieminen	Gilles Elseneer Jean-Michel Pequery	6–7(2–7), 6–4, 3–6
Win	2–2	Dec 2000	Prague, Czech Republic	Challenger	Hard	Aisam Qureshi	Ivo Heuberger Ville Liukko	6–4, 6–4
Win	3–2	Jul 2005	Campos do Jordão, Brazil	Challenger	Hard	Aleksandar Vlaski	Franco Ferreiro Marcelo Melo	7–6(7–5), 6–4
Win	4–2	Nov 2006	Rimouski, Canada	Challenger	Carpet	Frederik Nielsen	Jasper Smit Martijn van Haasteren	6–2, 6–4
Loss	4–3	Nov 2008	Rimouski, Canada	Challenger	Hard	Michael Ryderstedt	Milos Raonic Vasek Pospisil	7–5, 4–6, [6–10]

Singles