# 1999 Mercedes-Benz Cup – Singles

Andre Agassi was the defending champion, but was defeated in the final to Pete Sampras with a score of 7–6$^{(7–3)}$, 7–6$^{(7–1)}$. By reaching the final, Sampras completed his 271st week at the world No. 1 ranking in his career, surpassing the previous record of 270 weeks established by Ivan Lendl.

## Seeds

* Andre Agassi (final)
* Pete Sampras (champion)
* Tim Henman (first round)
* (n/a)
* Thomas Enqvist (second round)
* Goran Ivanišević (second round)
* Lleyton Hewitt (quarterfinals, retired)
* Wayne Ferreira (quarterfinals)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| 1 | Andre Agassi | 6 | 6 | | | | |
| | Andrew Ilie | 4 | 2 | | | | |
| | Andrew Ilie | 4 | 2 | 1 | Andre Agassi | 6$^3$ | 6$^1$ |
| | | | | 2 | Pete Sampras | 7$^7$ | 7$^7$ |
| Q | James Sekulov | 0 | 2 | 2 | Pete Sampras | 7$^7$ | 7$^7$ |
| 2 | Pete Sampras | 6 | 6 | | | | |

### Top half

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | A Agassi | 6 | 6 | | | | | | | | | | | | | |
| | JM Gambill | 2 | 2 | 1 | A Agassi | 6 | 6 | | | | | | | | | |
| Q | E Taino | 7$^7$ | 6 | Q | E Taino | 2 | 3 | | | | | | | | | |
| | L Paes | 6$^4$ | 1 | | | | | 1 | A Agassi | 5 | | | | | | |
| | D Nestor | 6$^5$ | 3 | | | | | 7 | L Hewitt | 4$^r$ | | | | | | |
| | A Pretzsch | 7$^7$ | 6 | | A Pretzsch | 3 | 1 | | | | | | | | | |
| WC | A O'Brien | 3 | 2 | 7 | L Hewitt | 6 | 6 | | | | | | | | | |
| 7 | L Hewitt | 6 | 6 | | | | | | | | | | 1 | A Agassi | 6 | 6 |
| LL | P Srichaphan | 2 | 1 | | | | | | | | | | | A Ilie | 4 | 2 |
| Q | M Larsson | 6 | 6 | Q | M Larsson | | | | | | | | | | | |
| | J Björkman | 4 | 4 | | A Dupuis | w/o | | | | | | | | | | |
| | A Dupuis | 6 | 6 | | | | | | A Dupuis | 7$^8$ | 4 | 4 | | | | |
| | B Black | 4 | 6$^8$ | | | | | | A Ilie | 6$^6$ | 6 | 6 | | | | |
| | A Ilie | 6 | 7$^{10}$ | | A Ilie | 6 | 6 | | | | | | | | | |
| | M Mirnyi | 3 | 3 | 6 | G Ivanišević | 4 | 4 | | | | | | | | | |
| 6 | G Ivanišević | 6 | 6 | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 5 | T Enqvist | 6 | 6 | | | | | | | | | | | | | | | |
| | M Woodforde | 3 | 4 | | 5 | T Enqvist | 7$^7$ | 4 | 3 | | | | | | | | | |
| | M Damm | 5 | 6 | 5 | Q | J Sekulov | 6$^1$ | 6 | 6 | | | | | | | | | |
| Q | J Sekulov | 7 | 4 | 7 | | | | | | Q | J Sekulov | 2 | 6 | 6 | | | | |
| | M Chang | 6 | 6 | | | | | | | | M Chang | 6 | 2 | 2 | | | | |
| | W Black | 3 | 1 | | | M Chang | 6 | 6 | | | | | | | | | | |
| | G Raoux | 6 | 7$^7$ | | | G Raoux | 4 | 2 | | | | | | | | | | |
| 3 | T Henman | 4 | 6$^4$ | | | | | | | | | | | | Q | J Sekulov | 0 | 2 |
| 8 | W Ferreira | 6 | 7$^7$ | | | | | | | | | | | | 2 | P Sampras | 6 | 6 |
| | G Grant | 4 | 6$^2$ | | 8 | W Ferreira | 5 | 7 | 6 | | | | | | | | | |
| | J Gimelstob | 6 | 6 | | | J Gimelstob | 7 | 5 | 2 | | | | | | | | | |
| WC | T Dent | 2 | 2 | | | | | | | 8 | W Ferreira | 6 | 3 | 3 | | | | |
| | S Lareau | 6 | 6 | | | | | | | 2 | P Sampras | 4 | 6 | 6 | | | | |
| Q | D Wheaton | 4 | 2 | | | S Lareau | 6$^5$ | 3 | | | | | | | | | | |
| WC | P King | 1 | 2 | | 2 | P Sampras | 7$^7$ | 6 | | | | | | | | | | |
| 2 | P Sampras | 6 | 6 | | | | | | | | | | | | | | | |