Kilmarnock played at three other sites (The Grange, Holm Quarry and Ward's Park) in their early years, before the club moved to Rugby Park in December 1877. This was not the precise site of the present stadium, as the field is now covered by Charles Street. The grounds were shared by cricket and rugby teams – sports which Kilmarnock had played previously – and the connection with rugby gave the ground its name. Rugby Park hosted its first international match in March 1894, when Scotland won 5–2 against Wales. By this time, the pitch had been moved to its current position. The ground was largely rebuilt and inaugurated with a match against then-champions Celtic on 26 August 1899, when Kilmarnock fought back from a 2–0 deficit to secure a draw. It was their first match in the top tier of Scottish football, having won the Second Division the previous season.
Originally, the ground was constructed with a running track around its edge, a pavilion and a stand along the west side. This layout meant that Rugby Park was similar to Ibrox Park, which opened four months later. The pavilion and stand were linked in 1914, which produced 1,900 seats in a total capacity of 20,000. In 1935 a cover was added to part of the south terrace. This terracing was later dubbed the Johnnie Walker stand, due to the company having an advert on the roof. During the Second World War, the British Army installed large oil storage tanks on the pitch. The club was not compensated, but Italianprisoners of war helped to extend the north terrace.Floodlights were installed and first used in an October 1953 friendly match against Manchester United. A roof was added to the east terrace in 1959, and the West (Main) Stand was renovated during the 1960–61 season. Rugby Park set its record attendance in March 1962, when 35,995 fans saw Kilmarnock lose 4–2 to Rangers in the 1961–62 Scottish Cup. This was a successful era for the club, as they finished runners-up in the league four times and won the league championship in 1964–65. Safety regulations cut the capacity of Rugby Park to 17,528 by the 1980s, but this figure was rarely troubled as the club fell to the Second Division. The Taylor Report, published in January 1990, recommended that British stadiums should become all-seater. Around the same time, a new board of directors took control of Kilmarnock. The new board initially proposed to move the club to an out-of-town site besides the A77 road as part of a wider development, but this was rejected by planning restrictions. The board then decided to redevelop Rugby Park. The last game before reconstruction was played on 7 May 1994, when Kilmarnock beat Rangers 1–0. During the 1994–95 season the capacity was significantly reduced as three new stands were constructed; the Moffat Stand, the Chadwick Stand and the East Stand. Their completion brought the capacity of the stadium to 18,128. The work was completed in just 348 days, as the new stands were first opened for a game against Rangers on 20 April. Kilmarnock officially opened the new Rugby Park on 6 August 1995, in a friendly match against English league championsBlackburn Rovers. Alan Shearer hit a hat-trick as the home team lost 5–0.
On 12 May 1998 Rugby Park hosted the last Ayrshire Cup final, as Kilmarnock fought back from 0–2 to beat Ayr United 4–2. In the summer of 1999, league regulations meant that Kilmarnock had to install undersoil heating at the ground. On 26 August of that year, Kilmarnock celebrated one hundred years at Rugby Park with a victory over KR Reykjavik in the 1999–2000 UEFA Cup.
Some work has since been done to increase the revenue created by the ground. In June 2002 the Park Hotel was opened adjacent to the stadium. The hotel was built on the site of Kilmarnock's training pitch and accommodates fifty twin/double bedrooms, a conference centre, a café, bar and restaurant. In November 2004 a new sports bar was opened in the West Stand, sponsored by Foster's Lager.
An artificial playing surface was installed in the summer of 2014. This was later replaced by an artificial hybrid surface during the 2019 close season. In February 2019 Kilmarnock received approval to install a new safe-standing section in areas of the East and Moffat stands. The installation process was completed in early December of that year.