Rypien was one of several players to benefit from the team's success following their championship season. The Redskins signed him to a 3-year, $9 million deal entering the 1992 season. However, the team battled age and injuries and finished the regular season with a 9–7 record, barely making the playoffs. His passing yardage was a respectable 3,282 yards, but his passer rating fell from 97.9 in 1991 to 71.7 in 1992 and his interceptions outnumbered his touchdowns 17–13. Although a dominant team performance in the playoffs brought victory over the Minnesota Vikings in an NFC Wild Card away game, the Redskins eventually lost on a rainy, muddy field in a bruising game vs. the San Francisco 49ers, and the Rypien era was essentially over. Under new head coach Richie Petitbon, Rypien had his best training camp in 1993 and expectations were high following a Monday Night win over the defending Super Bowl Champion Dallas Cowboys. However, Rypien injured his knee in Week 2 against the Arizona Cardinals and the team began a precipitous slide toward a 4–12 season finish.