Due to rapid technological advancement that continues to permeate almost all facets of the education sector, video learning has been explored to enhance performance, but most researchers do not incorporate flipped classroom in mathematical videos, which affects the teaching and learning of the subject in Nigeria. This study checked the effectiveness of video learning in flipped and flipped collaborative classroom on mathematics students' achievement and retention. Using a randomized controlled trial with repeated measures approach, 70 senior secondary school students were purposively sampled from two private secondary schools in Gombe State, Nigeria, out of which they were randomly assigned into two experimental groups: video learning flipped classroom and video learning flipped collaborative classroom (VLFCC). Data was obtained using a 30-item mathematics achievement test, which was validated and pilot-tested (r=0.93). Results were computed using descriptive statistics and two-way mixed design repeated measures analysis of variance. Findings revealed that while the students' within subject performance improved tremendously in the post-test after the four-week treatment, the students in VLFCC performed better in both achievement (F[1, 69]=1,576.362, p=0.000, effect size of ([partial eta-squared]) of 0.954) and retention (F[[subscript 1, 69]]=114. 119, p=0.000, with an effect size ([partial eta-squared]) of 0.785. The finding has some implications for it exposes mathematics teachers, researchers, and policy makers to the credence of deploying video learning in flipped collaborative classroom to improve students' performance by engaging students in collaborative learning in addition to watching pre-class videos, where students discuss in small groups in order to learn through observation, imitation, repetition and behavior modeling, thus making them to learn at their pace in order to construct their own knowledge.