Holland made his debut in the ski jumping world cup on December 3, 1989 in Thunder Bay . In the first three years in the World Cup, however, he remained without any points and no top placements. At the Nordic World Ski Championships in 1991 in Val di Fiemme , Holland reached 29th place on the normal hill and 52nd place on the large hill. On December 14, 1991 in Sapporo with 13th place he made the leap into the points for the first time. A day later he was even able to improve to 12th place. At the Four Hills Tournament 1991/92 Holland was able to jump into the points in three of four competitions and even achieved the best result of his career with 5th place in Garmisch-Partenkirchen . He finished the tour in 10th place in the tour's overall ranking. Because of this success he was part of the squad for the 1992 Winter Olympics in Albertville . There he reached the 13th place on the normal hill and 12th place on the large hill. Despite declining performance in the World Cup and the temporary change to the Ski Jumping Continental Cup , he was back in 1994 for the Olympic Winter Games in Lillehammer . There he only reached 48th place on the normal hill and 46th place on the large hill. After another unsuccessful year in the Continental Cup, Holland ended his active ski jumping career in 1995.
Jim Holland is the brother of the equally successful ski jumper Mike Holland and the Nordic combined athlete Joe Holland .