#2 Andriy Medvedev - 4 Masters 1000 titles
11-time titlist Andriy Medvedev won his only title of the 1997 season, and what turned out to be the last singles title of his career, at the Hamburg Masters.
The then 22-year-old beat Spaniard Felix Mantilla for the loss of just six games to win his third title at the tournament and the 4th Masters 1000 title of his career. He had previously triumphed at 1994 Monte Carlo, 1994 Hamburg and 1996 Hamburg.
In Grand Slam tournaments, Medvedev came within one set of his Major breakthrough at 1999 Roland Garros, conceding only three games in the first two sets against American Andre Agassi. But in a remarkable turnaround, Agassi took the next three sets 6-3, 6-4, 6-4 to become the first player in three decades to win the 'Career Grand Slam'.
#1 Marcelo Rios - 5 Masters 1000 titles
After making his Masters 1000 breakthrough at Monte Carlo 1997, Marcelo Rios won the Indian Wells - Miami 'Sunshine Double' in 1998.
The Chilean then followed up with the Rome Masters title later in the season. He lifted his fifth and last Masters 1000 title on the claycourts of Hamburg in 1999, with a five-set win over Mariano Zabaleta.
In his only appearance in a Grand Slam final, Rios went down to Petr Korda at the 1998 Australian Open. Rios also holds the rather ignominious record of being the only Slam-less World No. 1 in men's tennis history.