Skrepenak was drafted in the 1992 NFL Draft with the 32nd overall pick in the second round by the Los Angeles Raiders. He stayed with the franchise for four seasons, which included a relocation from Los Angeles to Oakland. During training camp of the 1993 NFL season he was moving into the starting lineup due to an injury to Gerald Perry. However, he was injured during his second preseason start when Charles Haley bull rushed him, which caused him to get tangled up between Jeff Hostetler and the turf and which resulted in a dislocated ankle joint that kept him out for the season. Skrepenak did not become a starter for the Raiders until midway through the 1994 NFL season when he replaced Bruce Wilkerson. He started the final 10 games of 1994 and the first 14 games of the 1995 NFL season before being benched toward the end of the season in favor of Robert Jenkins. Skrepenak was deactivated from the roster for the final two games of the season right before his contract expired. Officially, the deactivation was due to a combination of a rib injury and the flu, but some say it may have also been partially due to vocal play selection criticism. However, head coach Mike White and assistant coach Joe Bugel said the benching was merely a function of the full strength depth chart upon the return of Gerald Perry. Skrepenak was a vocal detractor on the organization after leaving the Raiders. Among the opinions Skrepenak expressed during his time with the Raiders was that the Raiders overemphasized slogans related to team history while setting penalty records as a team.