During his youth Matthews attended Ermington Public School and played for the Rydalmere Cricket Club, where he won the Under 11s Northern Districts Cricket Association Cricketer of the Year Award in 1970–71 and 1971–72. Coach Gordon Nolan was crucial to his early development.

Prior to his cricket career taking off, Matthews played Colts (under 20s) Rugby for the Eastwood Rugby Club and was a pro for the Cumbrian side Whitehaven Cricket Club for three seasons, starring in the club's 1981 league championship victory. At the conclusion of a successful season for Eastwood there was speculation that cricket may be put aside for Rugby, but he opted to play cricket.

1982/83: State Selection

Matthews made his first-class debut over the 1982–83 summer. Scoring 123 and taking 3-48 for the state colts against Queensland saw him selected in the New South Wales side to play Western Australia in November 1982, replacing John Dyson, who was on test duty.

He took 3-41 for NSW in a day-night game against a touring New Zealand side.

Some enterprising runs from Matthews in a game against Queensland helped NSW get in the Sheffield Shield final. Matthews played in the final, won by NSW—their first Sheffield Shield in 17 years.

He spent the 1983 winter playing club cricket in England.

1983/84: National Selection

Matthews was made 12th man for NSW's first game of the 1983–84 season—a delayed McDonald's Cup one day final. However, poor bowling by Murray Bennett in that game saw Matthews take Bennett's place.

He took three wickets in a shield game against WA, then scored 86 with 13 boundaries against the touring Pakistan side. He injured his hand while fielding in a game against Victoria. However, Matthews was then picked to play in the Australian team against Pakistan. He was chosen along with state teammate Murray Bennett.

Matthews had recently applied to go on the dole but was ruled out on a technicality when it was discovered that he was playing in a McDonald's Cup match that week. "I don't care what money I get, man", Matthews said. "It's the buzz of playing for Australia that's got me. I'm not worried about how much they pay ... I'd do it all for nothing just to wear that green cap." However, there was some sad news for Matthews. "My old coach from the Rydalmere junior days, Gordon Nolan, is dead and I owe so much to him that I wish I could have contacted him this morning as both our dreams came true."

Matthews was also picked to play in the Prime Ministers XI.

Matthews is a tough, useful, determined little cricketer; a steady, flat, off-spin bowler; a staunch, correct left-hand bat; and a