The 2004 NWC Conference Cross Country Champion, Hollingshead was a three-time All-America performer at Willamette, once in cross country and twice in track & field. In addition to his 2004 championship, Hollingshead finished fourth in the NWC in 2001 and 2002, followed by a second-place finish in 2003. His All-America recognition in cross country came from a 21st-place finish in 2003. In track & field, he was named the Athlete of the Meet at the 2005 NWC Championships after winning the 3,000-meter steeplechase and the 5,000-meter run. Nationally, he finished sixth in the steeplechase in 2004 and was second in 2005.  At the time of his induction, Hollingshead is #2 all-time at Willamette in the steeplechase at 9:01.55 and #3 at 8,000 meters in cross country with a time of 24:24.54.