In this study, the oxidation of di-iso-pentyl ether is investigated for the first time. Dilute mixtures (DIPEE/O2/N2) were oxidized in a jet-stirred reactor at 10 atm, between 450 and 1210 K and at a residence time of 0.7 s. Four mixtures were investigated with equivalence ratios of 0.5, 1, 2, and 4. In the low/intermediate temperature region, about 40 species were identified and quantified through FTIR and GC-FID-MS analyses. Given the quantified intermediates, it was observed that alkyl radicals such as iso-pentyl and iso-butyl radicals appear to be important intermediates in DIPEE oxidation. The most abundant oxygenated intermediates at low temperature include formaldehyde, iso-pentanal, acetaldehyde, and acetone which are reaching mole fractions greater than 100 ppm. Besides, species such as iso-butanal, isopentanoic acid, isoamyl formate, and isoamyl alcohol were also identified. DIPEE has very high reactivity (it starts to oxidize at 470 K) and exhibits two distinct zones of reactivity before the high-temperature zone, which can also be called as a double-cool flame. This behavior is due to the interactions caused by the low-temperature chemistry of the alkyl radicals within the cool flame regime. A detailed kinetic sub-mechanism for DIPEE oxidation was developed including detailed low-temperature chemistries of species like iso-pentanal and iso-butanal, based on our previous studies. While the kinetic mechanism predicts the experimental profiles reasonably well, there is room for improvement especially in assigning rate constants to the low-temperature reactions of the oxygenated species for which very few theoretically obtained or directly measured values exist.