Jeff Del Verne kicked field goals for the 1999 Wolverines early in the season. In fact, Del Verne led the team in scoring after 5 games. However, on October 9 (in the team's sixth game), Epstein tied Mike Gillette's November 19, 1988 Michigan record for longest field goal with a 56-yard kick against Michigan State in the Michigan–Michigan State football rivalry game. The kick was the longest ever by a Michigan State opponent at the time. It was the first successful field goal of Epstein's Michigan career (following two previous misses). On October 30, 1999, his 20-yard field goal with 18 seconds remaining clinched a 34–31 victory over Indiana for Michigan. That day would be Epstein's highest scoring day as a Wolverine (2–2 FGs and 4–4 in PATs). The game marked the first time that he handled the placekicking, kickoff and punting responsibilities. Of his seven kickoffs 3 were touchbacks and 3 more were covered inside the 20. Epstein punted six times, resulting in his first 50-yard punt and 2 punts landing inside the 20 yard line. For his efforts, he earned his first Big Ten Special Teams Player of the Week award. Epstein was the first player to handle placekicking, kickoff and punting responsibilities for Michigan since Mike Gillette in 1988. In overtime in the January 1, 2000 Orange Bowl against Alabama, his PAT provided the margin of victory (after he missed a 36-yard field goal at the end of regulation time). Epstein finished the season with 36 points (5–8 FGs and 21–22 PATs) and 32 punts for 1282 yards (40.1 average/7 inside 20).