The pair contrived to produce a stalemate during the regulation 90 minutes and the half an hour of extra time that followed.
Step forward Ward, the former island keeper saving two in the decisive penalty shoot-out as the Blackberry Lane side triumphed 4-2 on spot kicks.
Elsewhere St George’s beat Corinthians 2-1 despite being reduced to 10 men partly through the contest.
Laxey also remain in the hunt for the silverware after they beat Combi Two Douglas Royal 6-0 at Ballafletcher.
Second-tier Onchan edged past Douglas Athletic 4-3, while Youthie also disposed of higher ranked opposition beating Union Mills 6-1.
Holders Rushen eased into the next round with a 6-0 win at Ramsey, while Gymns beat Marown 5-1 in the other tie to go ahead.
Saturday, April 8
Ascot Hotel Junior Cup Prelim Round
Ramsey 0-6 Rushen
Douglas Royal 0-6 Laxey
RYCOB 6-1 Union Mills
Onchan 4-3 Douglas Athletic
Corinthians 1-2 St George’s
DHSOB 0-0 Peel AET Old Boys win 4-2 on penalties
Foxdale H-W Michael United Michael unable to field a team
Marown 1-5 Gymns
JCK Ltd Combination Two
Braddan 5-3 Castletown
Ascot Hotel Junior Cup first round draw
Ties to be played Saturday, April 22
RYCOB v Rushen United
Gymns v St John’s
Laxey v Onchan
Pulrose v Foxdale
St Mary’s v Castletown
St George’s v Governor’s Athletic
Colby v Douglas and District
Braddan v DHSOB