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The chemical investigation of the EtOH extract from the stem bark of <i>Trichilia monadelpha</i> (Thonn.) J. J. De Wilde afforded two new limonoids (<b>1</b> and <b>2</b>): 24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one (<b>1</b>) and (6<i>R</i>)-1-<i>O</i>-deacetylkhayanolide E (<b>2</b>), together with eleven known compounds (<b>3</b>–<b>13</b>), including additional limonoids, flavonoids, triterpenoids, steroids, and fatty acid. Their structures were determined using 1D- and 2D-NMR experiments, ESI mass spectrometry, and single crystal X-ray diffraction analysis. The antibacterial and antiplasmodial activities of the extracts, sub-extracts, fractions, and some of the isolated compounds were evaluated in known pathogenic strains, including <i>Staphylococcus aureus</i> and <i>Plasmodium falciparum</i>. Fraction E (<i>n</i>-Hex/EtOAc 30:70, <i>v</i>/<i>v</i>) showed significant activity against <i>S</i>. <i>aureus</i> ATCC 25923 with a MIC value of 3.90 µg/mL, while one of its constituents (epicatechin (<b>9</b>)) exhibited significant activity with MIC values of 7.80 µg/mL. Interestingly, grandifotane A (<b>6</b>) (IC₅₀ = 1.37 µM) and khayanolide D (<b>5</b>) (IC₅₀ = 1.68 µM) were highly active against the chloroquine-sensitive/sulfadoxine-resistant <i>plasmodium falciparum</i> 3D7 strain, unlike their corresponding plant extract and fractions.