Lori Littleton Cooling was the head coach of the St. Olaf softball program from 1995-2004 and led the Oles to a pair of Minnesota Intercollegiate Athletic Conference (MIAC) titles and one NCAA Tournament appearance.
After becoming St. Olaf's head coach at the age of 25, Littleton guided the Oles to the 1995 MIAC championship in her first season with a mark of 18-4 in conference. The 18 wins tied the program record for conference victories in a season.
The following year, St. Olaf won its second-straight conference championship and made its second appearance in the NCAA Tournament. The Oles finished the year 28-12 overall and 17-5 in the MIAC.
In 1997, St. Olaf won a program-record 31 games, finishing 31-12 overall and 18-4 in the MIAC. The Oles went a combined 71-17 in conference play over Littleton's first four seasons and she was named the MIAC Coach of the Year in both 1995 and 1996.
Over her 10 seasons, Littleton coached 19 All-MIAC selections and six NFCA All-Midwest Region honorees. St. Olaf went 168-207 (.448) overall and 111-108-1 (.507) in the MIAC during her 10 seasons leading the program.