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<i>Harposporium anguillulae</i>, an endoparasitic nematophagous fungus (ENF), is a model fungus from which the genus <i>Harposporium</i> was established. It can infect nematodes via ingested conidia. In this paper, the morphology and nematode–fungus interaction between <i>Panagrellus redivivus</i> and <i>H. anguillulae</i> were observed by scanning electron microscopy (SEM). The secondary metabolites of <i>H. anguillulae</i> were also studied. Seven metabolites were purified and identified from an ethyl acetate extract of broth and a methanol extract of mycelium. These include a new polyketone 5-hydroxy-3-(hydroxymethyl)-6-methyl-2<i>H</i>-pyran-2-one (<b>1</b>) and six known metabolites (17<i>R</i>)-17-methylincisterol (<b>2</b>), eburicol (<b>3</b>), ergosterol peroxide (<b>4</b>), terpendole C (<b>5</b>), (3β,5α,9β,22<i>E</i>)-3,5-dihydroxy-ergosta-7,22-dien-6-one (<b>6</b>), and 5α,6β-epoxy-(22<i>E</i>,24<i>R</i>)-ergosta-8,22-diene- 3β,7α-diol (<b>7</b>). These metabolites were assayed for their activity against plant root-knot nematode, <i>Meloidogyne incognita</i>, and the results showed that terpendole C (<b>5</b>) had weak nematicidal activity but also that other compounds did not have evident activity at a concentration of 400 μg mL⁻¹. Compound <b>1</b> exhibited an attractive effect towards <i>P</i><i>. redivivus</i>.