1988 - Signed on as Oldies 94.3 playing the oldies format. Original air personalities were Steve Cody, Skip Kelly, Donnie Pachine, Steve Street, Rock-n-Roll Joel, Patti Stevens, Barry West, Lorna O'Connell, and Lindy Rome.
1998 - Changed frequencies from 94.3 MHz to 105.5 MHz still playing oldies as KOOL 105.5. Line-up consisted of Skip Kelly, Mike Perry, Joe Steel, Russ Riba, and Rock-n-Roll Joel.
2000 - Dropped the oldies format for Adult Contemporary/Greatest Hits.
2002 - Started playing an annual broadcast of Christmas songs from the day after Thanksgiving till New Years Day.
2003 - The Mo & Sally Morning Show joined KOOL 105.5 from WJNA (they were on WRMF, and Mix 102.3 previously).
2005 - Tim Allan Walker joined The Mo & Sally Morning Show from 1290 WJNO/Air America Radio. KOOL 105.5 broadcasted a week of Hurricane Wilma recovery information spearheaded by The Mo & Sally Morning Show with Tim Allan. The station established itself as the clear community disaster recovery leader.
2007 - KOOL 105.5 dropped WPEC-TV as its news partner along with eleven other Clear Channel radio stations and became partners with WPTV-TV. Clear Channel also changed newspaper partnerships from the Palm Beach Post to the Sun Sentinel. Mike Perry exited the station for an afternoon drive gig in New York at Fresh 102.7. Tim Byrd joined the station in afternoons and Bobby Rich moved to middays. Bobby Rich exited and headed back to Tampa. Jennifer Agostino is named Program Director for WOLL (she is also the Program Director for WRLX) then later exits. Skip Kelly returned to take over midday duties.
Jennifer Agostino exited in October to pursue other interests. Jodi Stewart took the reins as Program Director. John Tesh was added to the line-up from 7pm-Mdnight 6 days a week.
2008 - Marked the return to the Palm Beach Post as the official newspaper of KOOL 105.5.