"Didn't We Almost Have It All" received positive reviews from the music critics, who praised its lyrics, production, and Houston's vocal performance.

A live performance from her September 2, 1987 concert in Saratoga Springs, New York was used as the official video and played on MTV, VH1, and BET.

[3] Los Angeles Times editor Robert Hilburn wrote, "Houston's stardom will be boosted most by "Didn't We Almost Have It All", a sweeping Masser-Will Jennings ballad with the kind of big, emotional finish that will make Liza and hundreds of other singers wish they had been given first crack at the song.

"[4] Pop Rescue noted it as "an 80s power ballad", adding that Houston's "vocals take centre stage" on the song.

[5] Rolling Stone's Vince Alleti wrote, "Masser reprises the show-tune schmaltz of "Greatest Love of All" in his even cornier "Didn't We Almost Have It All".

[7] St. Petersburg Times editors Eric Snider and Annelise Wamsley described "Didn't We Almost Have It All" as "an overblown tune co-written by Michael Masser (...) that finds Houston stripped of subtlety - with her wire-to-wire belting, you can just see the fetching songstress looking skyward, arms outstretched.

It also reached number two on the Hot Black Singles chart for one week (October 10, 1987), behind "(You're Puttin') A Rush on Me" by Stephanie Mills.