He made the semi-finals of Morocco's Grand Prix Hassan II and was a quarter-finalist at four tournaments, in San Marino, Sankt Pölten, Sicily and Majorca.

His best performances in 2000 included being a semi-finalist at the Swedish Open and making another quarter-final appearance in the International Raiffeisen Grand Prix at Sankt Pölten.

Hipfl bettered his previous two efforts at the Sankt Pölten tournament in 2001, making it into the final, which he lost to fellow wild card Andrea Gaudenzi.

In 2002, he reached another International Raiffeisen Grand Prix quarter-final and was also a quarter-finalist at the 2002 BellSouth Open, after which he attained his career high ranking of 63.

In 1999, he helped Austria qualify for the following year's World Group with a straight sets win over Sweden's Magnus Gustafsson, in the fifth and decisive rubber.