Lorenzo Veneziano
1359-66
The Madonna of Humility with Saints Mark and John the Baptist
National Gallery
The Virgin is represented here as the Madonna of Humility, seated on the ground, as in the paintings by Lippo di Dalmasio and from the
Dalmatian School.
She has a crescent moon at her feet, the remains of a roundel representing the sun on the neckline of her robe, and stars behind. These elements may be linked with the subject of the Immaculate Conception, a common theme in Venetian painting of this period.
Saint Mark at the left is identified by the inscription, and at the right Saint John the Baptist, dressed in skins, points to the Christ Child.

Lippo di Dalmasio
1390-1400
The Madonna of Humility
National Gallery
The Virgin Mary, who is seated in a flowery meadow, has a crown of twelve stars and the moon at her feet; the glory behind her represents her as 'clothed with the sun'. This corresponds to the protrayal of Mary as the Women of the Apocalypse, as described in the Book of Revelation (12: 1).
The work was probably painted in Bologna; it may have been a confraternity banner and appears always to have been on canvas.
Filippo Lippi
1452
Virgin with the Child and Scenes from the Life of St Anne
Galleria Palatina, Palazzo Pitti
Painted for a member of the Bartolini family. The bustle of activity around the bed of St Anne focuses the viewer's attention on the human aspects of Mary's birth.
In the background, St Anne embraces her husband as he returns to the house; the public city gate has been replaced by a scene of private affection.
I would be very interested to learn the original location of this work.

Vincenzo Foppa
c. 1470
Madonna of the Book
Museo d'Arte Antica del Castello Sforzesco, Milan
Intended for domestic devotions, this small (37.5 x 29.6 cm) work was created in the years immediately before Sixtus issued his
Bull establishing the feast of the Immaculate Conception.
Foppa has adopted the Flemish practice (see
next image) of surrounding the image with the devotional text.
The inscription on the frame reads AVE SANCTIS[S]IM[A] MARIA, PORTA PARADIXI, DOMINA MONDI, PURA SINGULARIS, TU ES VIRGO SINGULARIS TU CONCEPISTI IEXUM.

Alvise Vivarini
1480
Madonna and Child with Saints (Sacra Conversazione)
Gallerie dell'Accademia, Venice
Commissioned for the church of St. Francis in Treviso by Francesco Lanenigo. The saints on the left are Louis of Toulouse, Anthony of Padua and Anne; on the right stand Joachim, Francis and Bernardino. The introduction of Joachim and Anne into the scene, combined with the painting's strong Franciscan connections, have led to suggestions that reference is being made to the doctrine of the Immaculate Conception.
Thanks to Betty R-S for drawing my attention to this work.

Carlo Crivelli
1492
The Immaculate Conception
National Gallery
This may be the earliest dated picture of the Virgin of the Immaculate Conception. It was painted, soon after the
decrees of Sixtus IV marked the victory of the Franciscans in the long dispute, for the church of San Francesco in Pergola.
The lily in a pure crystal glass recalls the key text of the doctrine,
sicut lilium inter spinas (thou are the lily among thorns - Song of Songs 2:2).
Sicut lilum provided the title for
Nogarolo's Office.
At the top of the panel two angels crown the Virgin at the behest of God the Father and the Holy Spirit; the Coronation of the Virgin was the only other occasion when she was represented alone in an altarpiece.
Inscribed on the scroll held by the two angels is:
VT. INMENTE. DEI. ABINITIO. CONCEPTA. FVI. ITA. ET. FACTA. SVM.
(As from the beginning I was conceived in the mind of God, so have I in like manner been conceived in the flesh.)
The inscription relates alludes to the
belief that Mary, as the mother of the Saviour, existed in the mind of God before the formation of the world. It refers to a number of different verses: "The Lord possessed me in the beginning of his way, before his works of old," (Proverbs 8:22) "I was set up from everlasting, from the beginning, or ever the earth was," (Proverbs 8:23) and "He created me from the beginning before the world, and I shall never fail." (Ecclesiastes 24:9).

Matteo da Gualdo
1497
The Tree of Jesse
Museo Civico Rocca Flea, Gualdo Tadino
The top branches of the Tree of Jesse contain the Virgin's parents, Joachim and Anna. The tree sprouts from the supine body of Adam, who is covered with thorny branches, symbolising the bonds of Original Sin which his descendant, Mary, has escaped through her Immaculate Conception.
Thanks to Betty R-S for drawing my attention to this work.

Piero di Cosimo
1498
The Immaculate Conception
Uffizi
Painted for the Tedaldi chapel in SS. Annunziata, a church identified with the Medici family, and thus with the Dominican Order. However, the inclusion of St Antoninus, former bishop of Florence and an opponent of the doctrine, would seem to indicate that the dove was bringing peace as well as Immaculate Conception.
As the Holy Spirit descends on the Virgin, reminding the spectator of her own incarnation through divine intervention, the scenes associated with Christ's miraculous Incarnation unfold around her.
On her pedestal is a fictive relief of the Annunciation; to the left is the Annunciation to the shepherds and the Adoration of the Child, while to the right Mary and Joseph embark on the Flight into Egypt.
Flanking the Virgin are, on one side, Saints Catherine, John the Evangelist, and Filippo Benizzi. On the other are Saints Margaret, Peter and Antoninus.

Hugo van der Goes (follower)
c. 1500
Virgin and Child
National Gallery
On the wings of this small painting (48.3 x 38.1 cm) is inscribed, in Gothic script, a prayer to the Immaculate Virgin:
Ave/ Sanctissima/ Maria m[ate]r/ Dei Regina/ Celi porta/ Paradisi/ Domina/ Mu[n]di pura/ Singularis/ tu es Virgo/ Tu sine pec[cat]o/ Concepta/ concepisti/ J[e]h[su]m sine/ o[m]ni macula. Tu/ Peperisti,/ Creatorem/ et salvatore[m]/ Mundi/ In quo non/ Dubito/ libera me/ Ab omni/ malo Et/ Ora pro/ Peccato/ Meo/ Amen.
Hail, Most holy Mary, Mother of God, Queen of Heaven, Gate of Paradise, Mistress of the World, you are the one pure virgin; yourself conceived without sin you conceived Jesus without any stain. You have borne the Creator and Saviour of the World in whom I firmly believe. Deliver me from all evil, and pray for my sins. Amen.

Vincenzo di Antonio Frediani
1503
Disputation of the Immaculate Conception
Museo Nazionale di Villa Guinigi, Lucca
Painted for the Franciscan church of San Francesco in Lucca. Rife with quotations from
Bernardo di Busti's Office, litany symbols of the Virgin decorate the landscape. Saints and prophets display inscriptions and symbols drawn from the litanies. Saints Anselm, Augustine and Duns Scotus join David and Solomon with expositions of the Virgin's Immaculate Conception.
Each saint and prophet is labelled. St. Anthony of Padua's name is written under the figure of Scotus who had not been canonized at the time of the painting's execution. The discovery of a document relating to the commission verifies his identity.
The inscriptions from the litanies include
Plantatio Rose in Hiericho,
mirra electa, and
balsamus, while others are suggested by the cedar and palm trees in the background.

Jean Hey (Master of Moulins)
c. 1500
The Meeting at the Golden Gate and the Annunication
Meeting - National Gallery; Annunciation - Art Institue of Chicago
These are two surviving fragments of a
rectangular altarpiece. The subject of the central panel is unknown. On the right of the
National Gallery panel is the Emperor Charlemagne, included as if he were a saint. The
Chicago Annunciation (cut on the left edge) is likely to have included Saint Louis, who is often associated with Charlemagne in paintings.
As the left panel illustrates the miraculous Conception of the Virgin at the moment of her parents' embrace, and the right hand panel depicts the moment of the Incarnation of Christ, it is suggested that the panel is intended to expound the
doctrine of the Immaculate Conception.
It was painted for the altar of the Immaculate Conception in Moulins cathedral, with a central Virgin and Child or a Crucifixion.
Giotto to Durer page 358

Giovanni Bellini
c. 1513
Eight saints meditating on the mystery of the Virgin
San Pietro Martire, Murano, Venice
Mary is carried aloft on a cloud born by cherubs, observed by SS. Peter, John the Evangelist, Mark, Francis of Assisi, Louis of Tououse, Anthony Abbot, Augustine and John the Baptist.
Although this picture is conventionally seen as an Assumption, it is argued (Rona Goffen
Giovanni Bellini 1989) that it is non-narrative and represents the Immaculate Conception. The presence of only three apostles and several Franciscan saints is adduced in support of this theory.
The painting was originally on the high altar of the church of Santa Maria degli Angeli in Murano; it was commissioned in 1501 by Doge Agostino Barbarigo.
It is given this late date on stylistic grounds, by comparison to the figure of St Louis executed (1513) for the
altarpiece in San Giovanni Crisostomo in Venice.