| 18‑Oct‑1999 | Lyon | Carpet | QF | 22 | 2 | (8)Spadea d. (1)Yevgeny Kafelnikov [RUS] | 6-2 3-6 7-6(5) | | 1.07 | 7.2% | 3.1% | 40.2% | 74.4% | 53.4% | 7/10 | 2:03 |
| 4‑Oct‑1999 | Basel | Carpet | R32 | 19 | 2 | (2)Yevgeny Kafelnikov [RUS] d. Spadea | 6-3 7-5 | | 0.71 | 6.7% | 5.0% | 53.3% | 59.4% | 46.4% | 1/5 | 1:15 |
| 27‑Sep‑1999 | Grand Slam Cup | Hard | R16 | 19 | 9 | Richard Krajicek [NED] d. Spadea | 6-2 7-5 | | | | | | | | | |
| 16‑Aug‑1999 | Indianapolis | Hard | QF | 34 | 1 | Spadea d. (1)Pete Sampras [USA] | 6-4 3-6 RET | | 0.89 | 13.7% | 0.0% | 45.1% | 78.3% | 67.9% | 3/4 | 1:01 |
| 2‑Aug‑1999 | Canada Masters | Hard | R16 | 25 | 9 | (6)Todd Martin [USA] d. (12)Spadea | 6-3 7-6(3) | | 0.72 | 6.7% | 5.3% | 46.7% | 71.4% | 60.0% | 4/6 | 1:20 |
| 5‑Jul‑1999 | Gstaad | Clay | R16 | 29 | 5 | Spadea d. (1)Gustavo Kuerten [BRA] | 6-2 2-6 7-6(6) | | 0.98 | 6.5% | 4.6% | 50.0% | 72.2% | 50.0% | 11/14 | 1:48 |
| 24‑May‑1999 | Roland Garros | Clay | R64 | 35 | 5 | Spadea d. (5)Richard Krajicek [NED] | 6-1 6-2 6-4 | | 2.05 | 7.1% | 1.4% | 61.4% | 86.0% | 63.0% | 0/0 | 1:28 |
| 10‑May‑1999 | Rome Masters | Clay | R64 | 27 | 9 | Spadea d. (9)Mark Philippoussis [AUS] | 7-6(2) 4-6 6-1 | | 1.24 | 5.4% | 3.3% | 58.7% | 79.6% | 57.9% | 6/7 | 1:51 |
| 19‑Apr‑1999 | Monte Carlo Masters | Clay | R32 | 33 | 9 | Spadea d. (6)Karol Kucera [SVK] | 6-4 6-3 | | 1.17 | 0.0% | 4.7% | 57.8% | 67.6% | 48.1% | 0/2 | 1:30 |
| 15‑Mar‑1999 | Miami Masters | Hard | R64 | 41 | 3 | Spadea d. (3)Yevgeny Kafelnikov [RUS] | 6-7(6) 7-6(4) 6-2 | | 1.23 | 10.0% | 3.0% | 54.0% | 74.1% | 50.0% | 6/10 | 2:14 |
| 18‑Jan‑1999 | Australian Open | Hard | R16 | 44 | 6 | Spadea d. (5)Andre Agassi [USA] | 6-1 7-5 6-7(3) 6-3 | | | | | | | | | |