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The fungus <i>Xylaria</i> sp. Z184, harvested from the leaves of <i>Fallopia convolvulus</i> (L.) Á. Löve, has been isolated for the first time. Chemical investigation on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called fallopiaxylaresters A–C (<b>1</b>–<b>3</b>), and a new bisabolane-type sesquiterpenoid, named fallopiaxylarol A (<b>4</b>), along with the first complete set of spectroscopic data for the previously reported pestalotiopyrone M (<b>5</b>). Known pyranone derivatives (<b>6</b>–<b>11</b>), sesquiterpenoids (<b>12</b>–<b>14</b>), isocoumarin derivatives (<b>15</b>–<b>17</b>), and an aromatic allenic ether (<b>18</b>) were also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and α-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 ± 0.82% at a concentration of 50 μg/mL. The compounds <b>5</b>, <b>7</b>, and <b>8</b> displayed weak antibacterial activity against <i>Staphylococcus areus</i> subsp. <i>aureus</i> at a concentration of 100 μM.