The No. 4-ranked Hamilton-Wenham Regional High School boys tennis team will take on Austin Preparatory School in the first round of the postseason tournament on Monday.
The Generals will take on the No. 5 ranked Cougars at 3:30 p.m. on its home courts at Pingree Park in the quarterfinals of the Div. 3 North tournament.
Hamilton-Wenham ended the season at 10-3 and had a bye through the first round of the tournament.
Austin Prep (14-6) got to the quarterfinals with a 5-0 win over No. 12 Watertown on Sunday.
The winner of Monday's match will advance to the Div. 3 North semifinals to face the winner of Manchester-Essex versus Bedford which is being played in Manchester-by-the-Sea, also on Monday.