Cliftonville started the season finale on the front foot when Kirsty McGuinness wrong-footed stopper Ellie Scott to go narrowly wide.
Both teams canceled each other out as the half progressed, with the Reds gaining more possession but the Glentoran defense able to deal with any threat that arose.
Just after the half-hour mark, Charlotte Haven’s untimely cross found Kirsty McGuinness in good position, left-footed off target.
Haven, who recently won her first senior Northern Ireland cap, continued to be involved as the Reds went forward and Caitlin McGuinness put her on target before being fouled by teammate Vicky Carleton.
Immediately after the restart, Naomi McLaughlin had two chances in quick succession, but both went over the crossbar.
Glentoran defended resolutely and Cliftonville struggled to find spaces with Louise McDaniel and Caitlin McGuinness as scoring opportunities remained few and far between.
The Reds had their best chance in the 68th minute when Caitlin McGuinness gave Carleton a great chance, but she failed to get her effort on target.
In the last five minutes of the half, Mia Moore saw Maddie Harvey-Clifford off her line after Danielle Maxwell Kirsty and Caitlin McGuinness were unable to turn after good play and shot wide.
Chances remained high until the final seconds of extra time when Ellie Scott pulled off a superb save to deny Toni-Leigh Finnegan grabbing a late winner.
Jess Foy scored the opening penalty of the innings before Caitlin McGuinness missed her shot.
Demi Vance and Carleton both failed to convert before Aimee Kerr and Finnegan made mistakes.
Faye Loughan and Anna Rose Robinson swapped penalties before Bailie ended her career in style with a powerful effort.