[en] Peripherally metalated porphyrinoids are promising functional π-systems displaying characteristic optical, electronic, and catalytic properties. In this work, 5-(2-pyridyl)- and 5,10,15-tri(2-pyridyl)-B${}^{III}$-subporphyrins were prepared and used to produce cyclometalated subporphyrins by reactions with [Cp${}^{\ast <!--\; ???\; -->}$IrCl${}_2$]${}_2$, which proceeded through an efficient C−H activation to give the corresponding mono- and tri-Ir${}^{III}$ complexes, respectively. While the mono-Ir${}^{III}$ complex was obtained as a diastereomeric mixture, a C${}_3$-symmetric tri-Ir${}^{III}$ complex with the three Cp${}^{\ast <!--\; ???\; -->}$-units all at the concave side was predominantly obtained in a high yield of 90 %, which displays weak NIR phosphorescence even at room temperature in degassed CH${}_2$Cl${}_2$, differently from the mono-Ir${}^{III}$ complexes. (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim)