Wednesday played their first Christmas Eve match in 1883 against Walsall Town at Bramall Lane. Two seasons later in 1885, Wednesday played Heeley on Christmas Eve and Lockwood Brothers on Boxing Day (both draws).

The first Christmas Day match wasn't played until 1893, when Wednesday drew 1-1 with Bolton Wanderers at Bolton.
  Matches on Christmas Day then became a regular feature of the holiday period until the late 1950's. The final Xmas day match being a 4-4 draw with Preston at Hillsborough, followed by the return match at Preston (a 3-0 defeat) on Boxing Day.