His most productive season came in 1998, when he posted career numbers with a 19-8 record and a 3.51 earned run average in 233⅓ innings of work. The Astros once again prevailed in the NL Central that year, and they faced off against the San Diego Padres in the NLDS. In Game 2, he went seven innings while allowing two runs on four hits although he would receive a no-decision in the 5-4 walkoff win (the only one in the series for the Astros). He followed with a 16-14 mark and a 3.85 ERA in 1999, while leading the league with 35 starts for the 2nd straight year. For the third straight year the Astros made it to the playoffs, and he would be the starting pitcher in Game 1. Facing the Braves and their ace Greg Maddux, Reynolds pitched six innings and allowed one run on seven hits as he prevailed over the Braves 6-1 for his only postseason win. In Game 4, he would last just five innings while allowing nine hits and four runs in 7-5 loss.