For the first (and penultimate) time, teams were allowed to enter reserve teams into the competition. However, only Maccabi Tel Aviv took advantage of this, and its B "Nordia" team reached the quarter-finals, before falling to Maccabi Zikhron Ya'akov after a replay.
The draw for the first and the second rounds was held in mid-November 1928. The matches were supposed to be played on 1 December 1928, however, the match between Maccabi Tel Aviv and PGH was postponed to 15 December 1928, and was played on Hapoel Tel Aviv ground.
Matches were played on 2 February 1929, except for the match between Hapoel Haifa and Wireless Sarafand, which was postponed due to weather conditions and was played on 16 February 1929. The match between Maccabi "Nordia" Tel Aviv and Maccabi Zikhron Ya'akov went into a replay, which was played on 16 February 1929. The match was abandoned at the 65th minute due to the waterlogged pitch, with Maccabi Zikhron Ya'akov leading 2–1, and the result was confirmed as final.