| 8‑Nov‑1999 | Moscow | Carpet | R16 | 97 | 53 | Nicolas Escude [FRA] d. Kroslak | 6-1 3-6 6-3 | | 0.83 | 4.9% | 4.9% | 62.2% | 68.6% | 45.2% | 6/9 | 1:24 |
| 8‑Nov‑1999 | Moscow | Carpet | R32 | 97 | 87 | Kroslak d. Jan Siemerink [NED] | 5-7 7-6(3) 7-6(3) | | 1.04 | 5.2% | 3.7% | 59.3% | 71.3% | 63.6% | 5/6 | 2:31 |
| 18‑Oct‑1999 | Lyon | Carpet | R64 | 63 | 58 | Jan Michael Gambill [USA] d. Kroslak | 6-1 6-2 | | 0.47 | 6.3% | 12.5% | 64.6% | 58.1% | 23.5% | 4/8 | 0:56 |
| 13‑Sep‑1999 | Tashkent | Hard | R32 | 53 | 221 | (Q)Ivo Heuberger [SUI] d. (8)Kroslak | 6-2 RET | | 0.51 | 10.0% | 10.0% | 65.0% | 53.8% | 0.0% | 1/4 | 0:22 |
| 30‑Aug‑1999 | US Open | Hard | R32 | 58 | 10 | (10)Marcelo Rios [CHI] d. Kroslak | 6-3 6-4 6-4 | | 0.62 | 9.2% | 8.0% | 67.8% | 66.1% | 50.0% | 2/5 | 1:26 |
| 30‑Aug‑1999 | US Open | Hard | R64 | 58 | 80 | Kroslak d. Paul Goldstein [USA] | 5-7 6-4 6-4 6-3 | | 1.12 | 7.9% | 12.9% | 64.3% | 72.2% | 32.0% | 9/14 | 2:49 |
| 30‑Aug‑1999 | US Open | Hard | R128 | 58 | 312 | Kroslak d. (WC)Mashiska Washington [USA] | 6-1 2-6 7-6(3) 7-5 | | 1.01 | 2.0% | 8.6% | 65.1% | 71.7% | 39.6% | 7/11 | 2:48 |
| 23‑Aug‑1999 | Boston | Hard | R32 | 57 | 41 | (8)Jonas Bjorkman [SWE] d. Kroslak | 6-2 7-6(4) | | 0.77 | 6.6% | 3.9% | 69.7% | 67.9% | 34.8% | 5/8 | 1:25 |
| 16‑Aug‑1999 | Washington | Hard | QF | 71 | 16 | (6)Nicolas Kiefer [GER] d. (14)Kroslak | 6-4 6-3 | | 0.81 | 3.8% | 21.2% | 51.9% | 55.6% | 20.0% | 3/10 | 1:08 |
| 16‑Aug‑1999 | Washington | Hard | R16 | 71 | 5 | (14)Kroslak d. (3)Tim Henman [GBR] | 3-6 6-3 6-4 | | 1.04 | 4.5% | 5.6% | 67.4% | 65.0% | 48.3% | 2/6 | 1:44 |
| 16‑Aug‑1999 | Washington | Hard | R32 | 71 | 114 | (14)Kroslak d. Lorenzo Manta [SUI] | 7-5 7-6(3) | | 1.17 | 4.6% | 5.7% | 56.3% | 79.6% | 55.3% | 6/7 | 1:30 |
| 16‑Aug‑1999 | Washington | Hard | R64 | 71 | 327 | (14)Kroslak d. (Q)Ben Ellwood [AUS] | 6-2 6-4 | | 1.22 | 3.8% | 9.0% | 64.1% | 66.0% | 50.0% | 7/8 | 1:20 |
| 9‑Aug‑1999 | Cincinnati Masters | Hard | R64 | 71 | 48 | Jan Siemerink [NED] d. Kroslak | 6-1 6-2 | | 0.67 | 5.1% | 17.9% | 51.3% | 70.0% | 26.3% | 3/7 | 0:57 |
| 2‑Aug‑1999 | Canada Masters | Hard | R64 | 69 | 64 | Michael Chang [USA] d. Kroslak | 5-7 7-5 6-1 | | 0.62 | 10.2% | 8.2% | 50.0% | 69.4% | 44.9% | 7/11 | 1:55 |
| 26‑Jul‑1999 | Kitzbuhel | Clay | R64 | 66 | 113 | Adrian Voinea [ROU] d. Kroslak | 6-1 7-6(3) | | 0.76 | 5.6% | 16.7% | 46.3% | 80.0% | 37.9% | 0/3 | 1:08 |
| 19‑Jul‑1999 | Stuttgart Outdoor | Clay | R64 | 66 | 91 | (WC)Jens Knippschild [GER] d. Kroslak | 6-4 6-3 | | 0.70 | 6.0% | 10.7% | 56.0% | 72.3% | 29.7% | 8/12 | 1:13 |
| 5‑Jul‑1999 | Bastad | Clay | R32 | 69 | 113 | German Puentes [ESP] d. (8)Kroslak | 4-6 6-1 6-3 | | 0.80 | 3.8% | 8.8% | 57.5% | 63.0% | 35.3% | 7/13 | 1:25 |
| 21‑Jun‑1999 | Wimbledon | Grass | R128 | 67 | 10 | (12)Carlos Moya [ESP] d. Kroslak | 6-4 7-5 6-2 | | 0.81 | 4.6% | 8.3% | 57.4% | 64.5% | 43.5% | 11/16 | 1:34 |
| 14‑Jun‑1999 | s Hertogenbosch | Grass | R16 | 67 | 32 | (6)Jonas Bjorkman [SWE] d. Kroslak | 7-5 6-2 | | 0.80 | 12.3% | 8.8% | 56.1% | 68.8% | 48.0% | 1/4 | 1:15 |
| 14‑Jun‑1999 | s Hertogenbosch | Grass | R32 | 67 | 163 | Kroslak d. (WC)Rogier Wassen [NED] | 6-4 6-2 | | 1.27 | 4.3% | 8.7% | 50.7% | 60.0% | 50.0% | 11/14 | 1:08 |
| 7‑Jun‑1999 | Halle | Grass | R32 | 68 | 32 | Jonas Bjorkman [SWE] d. Kroslak | 6-4 6-3 | | 0.74 | 9.2% | 12.3% | 61.5% | 72.5% | 40.0% | 6/9 | 1:10 |
| 24‑May‑1999 | Roland Garros | Clay | R128 | 66 | 31 | Marat Safin [RUS] d. Kroslak | 6-2 4-6 6-3 3-6 6-2 | | 0.89 | 4.4% | 8.8% | 57.4% | 62.8% | 41.4% | 13/22 | 2:28 |
| 17‑May‑1999 | St. Poelten | Clay | R16 | 67 | 26 | (5)Mariano Zabaleta [ARG] d. Kroslak | 7-5 6-3 | | 0.80 | 0.0% | 3.1% | 64.6% | 47.6% | 39.1% | 5/11 | 1:17 |
| 17‑May‑1999 | St. Poelten | Clay | R32 | 67 | 48 | Kroslak d. Jiri Novak [CZE] | 7-6(4) 7-5 | | 1.06 | 3.2% | 10.6% | 60.6% | 64.9% | 32.4% | 5/10 | 1:41 |
| 3‑May‑1999 | Hamburg Masters | Clay | R64 | 67 | 181 | (Q)Marco Meneschincheri [ITA] d. Kroslak | 1-6 7-5 6-4 | | 1.11 | 6.3% | 5.2% | 68.8% | 63.6% | 50.0% | 6/11 | 1:47 |
| 26‑Apr‑1999 | Prague | Clay | R32 | 65 | 267 | (Q)Eduardo Nicolas [ESP] d. Kroslak | 6-2 6-0 | | 0.40 | 0.0% | 9.2% | 64.6% | 50.0% | 26.1% | 7/13 | 0:58 |
| 12‑Apr‑1999 | Tokyo | Hard | R64 | 69 | 111 | Mikael Tillstrom [SWE] d. (13)Kroslak | 7-6(4) 6-4 | | 0.97 | 4.1% | 11.0% | 61.6% | 71.1% | 42.9% | 4/7 | 1:24 |
| 5‑Apr‑1999 | Hong Kong | Hard | R32 | 67 | 26 | (5)Nicolas Kiefer [GER] d. Kroslak | 6-1 6-0 | | 0.44 | 2.9% | 31.4% | 34.3% | 41.7% | 30.4% | 2/7 | 0:52 |
| 15‑Mar‑1999 | Miami Masters | Hard | R32 | 70 | 74 | Sebastien Grosjean [FRA] d. Kroslak | 6-2 6-4 | | 0.47 | 4.2% | 8.3% | 56.3% | 66.7% | 47.6% | 1/4 | 0:58 |
| 15‑Mar‑1999 | Miami Masters | Hard | R64 | 70 | 18 | Kroslak d. (17)Thomas Johansson [SWE] | 7-6(6) 2-6 6-3 | | 0.99 | 5.8% | 9.1% | 58.7% | 69.0% | 44.0% | 10/14 | 2:18 |
| 15‑Mar‑1999 | Miami Masters | Hard | R128 | 70 | 227 | Kroslak d. (Q)Ronald Agenor [USA] | 6-4 6-4 | | 1.58 | 6.3% | 16.7% | 47.9% | 87.0% | 56.0% | 1/3 | 1:13 |
| 1‑Mar‑1999 | Copenhagen | Carpet | R32 | 70 | 121 | (LL)Bernd Karbacher [GER] d. Kroslak | 6-3 6-4 | | 0.85 | 9.8% | 8.2% | 67.2% | 68.3% | 40.0% | 4/7 | 1:14 |
| 22‑Feb‑1999 | London | Carpet | R16 | 79 | 41 | Dominik Hrbaty [SVK] d. (Q)Kroslak | 6-2 6-3 | | 0.66 | 7.5% | 3.8% | 73.6% | 56.4% | 50.0% | 0/4 | 0:50 |
| 22‑Feb‑1999 | London | Carpet | R32 | 79 | 7 | (Q)Kroslak d. (2)Tim Henman [GBR] | 2-6 7-6(8) 6-4 | | 0.94 | 3.9% | 2.0% | 52.9% | 64.8% | 58.3% | 3/6 | 2:02 |
| 15‑Feb‑1999 | Rotterdam | Carpet | R32 | 81 | 174 | (WC)Edwin Kempes [NED] d. (Q)Kroslak | 6-4 7-6(1) | | 0.73 | 16.2% | 5.9% | 79.4% | 74.1% | 35.7% | 2/4 | 1:08 |
| 8‑Feb‑1999 | St. Petersburg | Carpet | R32 | 82 | 192 | (Q)Fredrik Jonsson [SWE] d. Kroslak | 6-1 7-6(3) | | 0.55 | 8.6% | 5.7% | 61.4% | 69.8% | 40.7% | 7/10 | 1:10 |
| 18‑Jan‑1999 | Australian Open | Hard | R32 | 89 | 16 | (14)Mark Philippoussis [AUS] d. Kroslak | 3-6 6-3 6-4 6-1 | | 0.57 | 5.3% | 5.3% | 63.2% | 63.1% | 51.0% | 3/8 | 1:57 |
| 18‑Jan‑1999 | Australian Open | Hard | R64 | 89 | 36 | Kroslak d. Mariano Puerta [ARG] | 3-6 4-6 7-6(4) 6-4 6-1 | | 1.14 | 7.2% | 3.0% | 71.1% | 72.0% | 47.9% | 9/13 | 3:04 |
| 18‑Jan‑1999 | Australian Open | Hard | R128 | 89 | 72 | Kroslak d. Juan Antonio Marin [CRC] | 6-1 7-6(1) 7-6(5) | | 1.49 | 7.7% | 2.9% | 70.2% | 72.6% | 51.6% | 2/6 | 2:05 |