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The 1987–88 season was Arsenal's 68th season in the top flight of English football. After finishing fourth in the league and winning the Football League Cup a year earlier, they slipped to finish sixth this season. They did reach the League Cup final again, and took a 2–1 lead against Luton Town at Wembley before missing a penalty which would have given them a 3–1 lead, and ended up losing the game 3–2. Arsenal were quarter-finalists in the FA Cup.
In the league, Arsenal got off to a slow start, winning just one of their first five games, before going top of the table with a 10-match winning run. However, they then went into freefall, winning just one of their next 11 league games, and although their form improved during the final four months of the season, they could only manage a sixth-place finish.
A new signing at the start of the season was Nigel Winterburn, who arrived from Wimbledon to fill the right-back position left vacant by the sale of Viv Anderson to Manchester United. Arsenal had agreed an £850,000 deal for Leicester City striker Alan Smith two months before the end of the previous season, although he had remained on loan back at the East Midlands club until the end of the campaign. Smith finished as Arsenal's top scorer in his first season at the club, finding the net 16 times in all competitions.
New signings at the club late in the season were defenders Lee Dixon and Steve Bould, as well as winger Brian Marwood. Young midfielders Michael Thomas and Paul Merson became regular members of the first team during this season, while at the end of the campaign defender Tony Adams, still only 21, succeeded Kenny Sansom as captain.
