The club was founded out of Oswestry Cricket Club on 4 September 1875; it claimed a foundation date of 1870 which may have been the date of the cricket club's foundation. Oswestry reached the semi-final of the first
Shropshire Senior Cup in 1877–78, and were drawn to visit
the original Shrewsbury club. The original tie ended in a 2–2 draw, with Oswestry's forward Alexander Fletcher Jones - a former student at Oswestry School but by now a
mathematics master at
Clifton College - being picked out as "an admirable centre". but the week before the replay, Jones was killed in an extraordinary incident while accompanying the College's cadet corps on the
Avonmouth Railway; one of the pupils, Edward Hemming, accidentally discharged a gun in one carriage, and the bullet struck Jones - in another carriage - in the chest. Oswestry went down 3–0 in the replay (also at Shrewsbury), its players wearing black armbands. The club gained a boost in 1878, when
Druids temporarily folded, which resulted in so many Druids players joining Oswestry, that Oswestry provided the majority of the
Welsh national side which narrowly lost 2–1 at
England in January 1879. It entered the
FA Cup for the first time in
1882–83, borrowing several players from the rival
Oswestry White Star club for the first round tie with the revived Druids, although to no avail as the Shropshire side bowed out. By the 1883–84 season, Oswestry F.C. absorbed the White Star, briefly using the White Star name for the Oswestry second XI. The club promptly went on its best run in
that season's FA Cup, when it reached the third round (last 28), and had the honour of hosting
Queen's Park, the highlight of the game for the home support being W. T. Foulkes equalizing an early Spiders goal, but the superior Scottish side ran out 7–1 winners, and Oswestry held a public dinner in honour of its conqueror at the Wynnstay Arms that evening. Its appearance in the
1885–86 FA Cup was not so convivial, its second round tie at home to
Crewe Alexandra kicking off late because of a dispute between Oswestry players and committee, which led to a number of players going on strike, and an XI only being rounded up late. The game ended 1–1, but because of the kick-off delay, and a 15 minute hold-up while Oswestry's Foulkes and Alexandra's Conde indulged in a lengthy punch-up, the referee declared it too dark to play extra-time, and the
Football Association disqualified Oswestry, due to the club's late arrival. Oswestry entered the
Welsh Cup from its first edition in
1877–78 until
1891–92. Its greatest achievement came in
1883–84, when it became the first English club to win the competition, beating Druids 1–0 in a replay at
Wrexham, the goal due to "the joint efforts of Farmer and Shaw", after an initial 0–0 draw. The two sides met again in the
1884–85 Welsh Cup final, but Druids gained revenge with a 3–1 win, thanks to two extra-time goals, after both original match and replay had ended 1–1 after 90 minutes. For the club's final Welsh Cup entry, it was drawn to visit
Chirk AAA, but scratched, and never appeared again. It was succeeded by
Oswestry United. ==Colours==