Chelsea have played Workington Town 3 times in competitive football, winning 2, drawing 1 and losing 0, first meeting on 24 Oct 1960 and most recently on 16 Dec 1964. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 24 Oct 1960 | 1960–61 | League Cup | H | Workington Town | 4–2 | John Mortimore, Peter Brabrook, Tony Nicholas, Bobby Tambling | 5,630 |
| 25 Nov 1964 | 1964–65 | League Cup | A | Workington Town | 2–2 | Barry Bridges 12, Barry Bridges 34 | 18,000 |
| 16 Dec 1964 | 1964–65 | League Cup | H | Workington Town | 2–0 | Peter Osgood 82, Peter Osgood 84 | 7,936 |