The title appears to be a hybrid of several similarly named shows and episodes:
A long-running documentary series about prison life. It does have a Season 14, but its ninth episode is not titled "Check In and Check Out". [S14E9] Check In and Check Out
There is no widely recognized television series or film that features a Season 14, Episode 9 titled This specific combination of season, episode number, and title does not appear in major television databases like IMDb or TV Guide. The title appears to be a hybrid of
Check It Out Season 1 Episodes * 1985-1988. * 3 Seasons. * D.L. Taffner Syndication Sales. * Comedy. TVGuide.com Check It Out (TV Series 1985–1988) - Episode list - IMDb [S14E9] Check In and Check Out