Dicks made his debut for West Ham on 2 April 1988 in a Division One game against Sheffield Wednesday. West Ham lost the game 2–1. He would go on to make eight appearances in the 1987-88 season, his first season with West Ham. The following season, he became a regular player and first choice left back for The Hammers, starting the first game of the season, a 4–0 away defeat to Southampton and playing 34 of a possible 38 games that season. The season also saw his first goal for the club in a 2–1 defeat at Highbury to Arsenal. It was a poor season for West Ham who were relegated to Division Two having finished one place off the bottom of the league in 19th place with 38 points. Relegation had seen the sacking of manager John Lyall and the appointment of Scot, Lou Macari. The new manager and Dicks exhibited a poor working relationship from the outset. Despite this, and with West Ham now playing second-tier football, Dicks retained his left back position and became their regular penalty taker following the exit of former first choice taker, Ray Stewart. Dicks became well known for his penalties. During his West Ham career he scored 35, missing four. His first penalty success came on 23 September 1989 proving to be the only goal in a win against Watford. A future regular captain of the West Ham side, this season also saw his first captaincy, in a League Cup game on 19 September 1989 against his former club, Birmingham City, with manager Macari telling him "I'm making you captain today and I'm making you penalty taker too". Dicks was often cautioned and sent off by referees. His first red-card was in a match versus Wimbledon in the Football League Cup in the 1989–90 season. It was an infamous encounter which included an on-pitch brawl between the opposing players. The fighting was sparked by a two-footed tackle by Wimbledon player, Dennis Wise on Dicks. Six players were booked with the game being described as "a disgrace to football" by journalist, Brian Woolnough. West Ham finished 7th in a season which saw the departure of Lou Macari and the appointment of former player, Billy Bonds as manager. Dicks and Bonds both had reputations as "hard men" and quarrelled frequently.